Novel quaternary ammonium compounds

ABSTRACT

[Object] To provide a medicine useful for treatment and prevention of hyperlipidemia, further for the treatment and prevention of cholestasis-accompanying hepatopathy, particularly primary biliary cirrhosis and primary sclerosing cholangitis, and for the treatment and prevention of obesity and fatty liver. 
 
[Means] A benzothiazepine compound represented by the following formula (1), having a thioamide bond and a quaternary ammonium substituent.

DETAILED DESCRIPTION OF THE INVENTION

1. Field of the Invention

The present invention relates to novel benzothiazepine compounds having a thioamide bond and a quaternary ammonium substituent and to pharmaceutical compositions that contain them.

2. Prior Art

Hyperlipidemia means a state-where neutral fat, cholesterol and the like in blood are at higher levels than the normal levels and has been known to deserve a treatment since it is a main risk factor in ischemic diseases. Further, hyperlipidemia is also known to cause arteriosclerosis and in particular, to decrease blood cholesterol level is effective for the prevention and treatment of arteriosclerosis. Arteriosclerosis is also known as a cause of myocardial infarction, cerebral thrombosis, peripheral arterial obstruction, and arteriosclerosis obliterans. Syndrome X was advocated by Reaven et al. (“Diabetes”, 37, 1595-1607, 1988) and means a multiple risk factor syndrome that develops arteriosclerosis by accumulation of risk factors such as hyperinsulinemia, hyperlipidemia, hypertension, and abnormality of glucose tolerance on an individual, although the factors are not so serious as to indicate the conditions of diseases when they exist independently of each other. A cholesterol-lowering agent is considered to be effective for the prevention or treatment of these diseases (Japan Clinical Hyperlipidemia—Volume 1—ISSN0047-1852).

At present, commercially available drugs for the treatment of hyperlipidemia include HMG-CoA reductase inhibitor drugs, anion exchange resin drugs and so forth. These drugs are used for the prevention and treatment of hyperlipidemia, in particular, hypercholesterolemia and arteriosclerosis. Furthermore, these drugs are also used in the prevention or treatment of myocardial infarction, cerebral thrombosis, peripheral arterial obstruction, and arteriosclerosis obliterans, which are diseases caused by hypercholesterolemia or arteriosclerosis.

HMG-CoA reductase inhibitors inhibit the activity of HMG-CoA reductase, resulting in a decrease in the amount of cholesterol in the liver, so that the low density lipoprotein (LDL) receptors in the liver increase and incorporate cholesterol in blood into the liver to decrease the cholesterol level (see Science, 232, 34, 1986). At present, the HMG-CoA reductase inhibitors have become standard drugs in medical therapy for the treatment of hyperlipidemia.

Further, cholestyramine, an example of an anion exchange resin, prevents the reabsorption of bile acid in intestines by adsorbing bile acid in the bowel. This results in increased synthesis of bile acid from cholesterol in the liver. As a result, LDL receptors increase in the liver and incorporate LDL cholesterol in blood into the liver, thereby lowering the cholesterol value (Reichner, E., et al., Journal of Lipid Research, 31, 2219-2226, 1990).

Primary biliary cirrhosis (PBC) is a disease, a major pathological condition of which is cholestasis in the liver due to chronic nonsuppurative, destructive cholangitis in the bile duct or due to loss of the bile duct. Symptoms based on this include fatigue, skin itching, icterus and the like (see Naika Sogo Shi (Medical Practice), 19, 987-992, 2001). Primary sclerosing cholangitis (PSC) is a disease attributable to inflammatory constriction of the bile duct and symptoms that accompany chronic cholestasis (fatigue, skin itching and so on) occur (KAN TAN SUI, 42, 559-568, 2001). No effective therapeutic methods have been established for both the diseases; however, ursodeoxycholic acid is usually believed to be most effective and thus used in clinical (Poupon R., et al., N. Engl. J. Med., 330, 1342-1347, 1994 and Mitschell, S A. et al., Gastroenterology, 121, 900-907, 2001). In addition, both the diseases are hepatopathy accompanying cholestasis and anion exchange resins such as cholestyramine and so forth are used for improving skin itching (Heathcote J. J. Gastroenterol Hepatol., 11, 605-609, 1996). Anion exchange resins are considered to exhibit their effect by adsorbing lipid-soluble substances including cholesterol and bile acid to inhibit the incorporation of these substances into the body (Thompson W G, Can. Med. Assoc. J., 104, 305-309, 1971). However, cholestyramine is used in a large dosage at a time because of being a resin, so that there occurs adsorption of vitamins, minerals, drugs and so forth. Further, they readily cause gastrointestinal complications such as obstinate constipation, so that in some cases it becomes difficult to continue taking the drug. In addition, its effectiveness is not satisfactory and it remains to be used only in a limited manner in clinical.

In recent years, ileal bile acid transporter inhibition has been suggested as a method different from that cholestyramine that inhibits circulation of bile acid from the bowel to the liver (The Journal of Biological Chemistry, 268, 18035-18046, 1993). In addition, International Patent Applications WO93/16055 and WO02/08211 and the like disclose compounds having ileal bile acid transporter inhibiting activity. From this it has been expected that if the ileal bile acid transporter is inhibited, the same pharmacological effects as those of cholestyramine can be obtained. Based on this background, it has been attempted to find an ileal bile acid transporter inhibitor that serves as a drug for the treatment and prevention of hyperlipidemia. However, the effectiveness of the compounds described in International Patent Applications WO93/16055 and WO02/08211 on hepatopathy accompanying cholestasis such as primary biliary cirrhosis and primary sclerosing cholangitis have not been shown yet.

[Means to Solve the Problems]

It has heretofore been demanded to provide novel drugs useful as therapeutic and prophylactic agents for hyperlipidemia, and furthermore drugs that are also useful as therapeutic and prophylactic agents for cholestasis-accompanying hepatopathy, in particular primary biliary cirrhosis and primary sclerosing cholangitis, as well as drugs that are useful as therapeutic and prophylactic agents for obesity, and fatty liver.

[Means for Solving the Problem]

To solve the above-mentioned problem, the inventors of the present invention synthesized various compounds and studied their activity. As a result, they have verified that novel benzothiazepine compounds represented by formula (1) below having a thioamide bond and a quaternary ammonium substituent have high therapeutic and preventive effects for hyperlipidemia and further extremely potent ileal bile acid transporter inhibiting activity and blood cholesterol lowering activity, so that they can be used as cholesterol lowering agents, in particular as a therapeutic agent and preventive agent for hyperlipidemia, arteriosclerosis, syndrome X, etc. Furthermore, the inventors have verified that the novel benzothiazepine compounds have therapeutic and preventive effects for cholestasis-accompanying hepatopathy, so that the compounds can be used as therapeutic and preventive agents for cholestasis-accompanying hepatopathy, particularly for primary biliary cirrhosis and primary sclerosing cholangitis. Also, the inventors have verified that the compounds can be used as therapeutic and preventive agents for obesity and fatty liver.

That is, the present invention provides a compound represented by formula (1) below.

[wherein R¹ and R², which may be mutually different, each represents an alkyl group having from 1 to 10 carbon atoms;

-   -   m represents an integer of 1 or 2, and R³ and R⁴, which may be         mutually different, each represents an alkyl group having from 1         to 5 carbon atoms;     -   Y represents any one of —NHCS—, —NHCSNH—, and —NHCSO—; where the         —NH in the —NHCS— represents a bond that links with an adjacent         benzene ring and the CS— in the —NHCS— represents a bond that         links with an adjacent Z, and the —NH in the —NHCSO— represents         a bond that links with an adjacent benzene ring and the CSO— in         the —NHCSO— represents a bond that links with an adjacent Z;     -   Z—(N⁺R⁵R⁶R⁷)_(n) represents an alkyl group or alkenyl group         having from 2 to 10 carbon atoms that is substituted with n         (—N⁺R⁵R⁶R⁷)s, where at least one of methylenes that constitute Z         may be replaced by any one of a phenylene and an —O—; n is an         integer of 1 or 2; and N⁺R⁵R⁶R⁷ is any one of I), II), and III)         below that are mutually independent;     -   I) R⁵, R⁶, and R⁷ may be mutually different and each represents         an alkyl group, alkenyl group, or alkynyl group having from 1 to         10 carbon atoms, where the alkyl group, the alkenyl group, and         the alkynyl group may be substituted with at least one of a         phenyl group, a naphthyl group, a pyridyl group, a quinolyl         group, a thienyl group, a furyl group, a piperidyl group, a         pyrrolidyl group, a morpholyl group, a cycloalkyl group having         from 3 to 7 carbon atoms, a cyano group, a nitro group, a         hydroxyl group, an oxo group, a thioxo group, a carboxyl group,         a —CONH₂ group, an —SO₃H group, and further, at least one of         methylenes that constitute the alkyl group, the alkenyl group,         and the alkynyl group may be replaced by any one of a phenylene,         a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an         —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—         where R⁸ represents an alkyl group or alkenyl group having from         1 to 5 carbon atoms and the alkyl group and alkenyl group of R⁸         may be substituted with at least one of a phenyl group, a         cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl         group; R⁹ and R¹⁰, which may be mutually different, each         represents an alkyl group or alkenyl group having from 1 to 5         carbon atoms and may be substituted with at least one of a         phenyl group, a cycloalkyl group having from 3 to 7 carbon         atoms, and a hydroxyl group; and W represents a counter anion,     -   II) N⁺R⁵R⁵R⁷ represents a monocyclic ring or bicyclic ring that         is formed by 4 to 9 carbon atoms in addition to an ammonium         nitrogen atom, provided that the position of its bonding with Z         is at the ammonium nitrogen atom, where one of the carbon atoms         that constitute the ring in the monocyclic ring and bicyclic         ring may be replaced by any one atom of oxygen, nitrogen, and         sulfur, and further, the monocyclic ring and the bicyclic ring         may be substituted with at least one of a hydroxyl group, an oxo         group, a thioxo group, a cyano group, a phenyl group, a naphthyl         group, a thienyl group, a pyridyl group, a cycloalkyl group         having from 3 to 7 carbon atoms, a carboxyl group, a —CONH₂         group, an —SO₃H group, and an —R¹¹ group; R¹¹ represents an         alkyl group or alkenyl group having from 1 to 8 carbon atoms,         where the alkyl group and the alkenyl group represented by R¹¹         may be substituted with at least one of a phenyl group, a         naphthyl group, a pyridyl group, a quinolyl group, a thienyl         group, a furyl group, a piperidyl group, a pyrrolidyl group, a         morpholyl group, a cycloalkyl group having from 3 to 7 carbon         atoms, a cyano group, a nitro group, a hydroxyl group, an oxo         group, a thioxo group, a carboxyl group, a —CONH₂ group, and an         —SO₃H group; further, at least one of methylenes that constitute         the alkyl group and the alkenyl group may be replaced by any one         of a phenylene, a thienylene, a furylene, a cyclohexylene, a         cyclopentylene, an —O—, an —S—, a —CO₂—, an NHCO—, an —NR⁸—, and         an —N⁺W⁻R⁹R¹⁰—, where R⁸, R⁹, R¹⁰, and W⁻ are as described         above; among R⁵, R⁶, and R⁷, those groups that are not involved         in formation of the monocyclic ring and the bicyclic ring are         the same as those in 1) described above,     -   III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring,         or an isoquinolinium ring, provided that the position of its         bonding with Z is at the ammonium nitrogen atom; the pyridinium         ring, the quinolinium ring, and the isoquinolinium ring may be         substituted with at least one of a cyano group, a nitro group, a         phenyl group, a naphthyl group, a thienyl group, a pyridyl         group, a cycloalkyl group having from 3 to 7 carbon atoms, an         alkoxy group having from 1 to 5 carbon atoms, a carboxyl group,         a —CONH₂ group, an —SO₃H group, and an —R¹² group where R¹²         represents an alkyl group or alkenyl group having from 1 to 9         carbon atoms; and the alkyl group and the alkenyl group         represented by R¹² may be substituted with at least one of a         phenyl group, a naphthyl group, a pyridyl group, a quinolyl         group, a thienyl group, a furyl group, a cycloalkyl group having         from 3 to 7 carbon atoms, a cyano group, a nitro group, a         hydroxyl group, an oxo group, a thioxo group, a carboxyl group,         a —CONH₂ group, and an —SO₃H group; and further, at least one of         methylenes that constitute the alkyl group and the alkenyl group         may be replaced by any one of a phenylene, a thienylene, a         furylene, a cyclohexylene, a cyclopentylene, an —S—, a —CO₂—, an         —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—, where R⁸, R⁹, R¹⁰, and W⁻         are as described above and X⁻ represents a counter anion]]

Further, each of the substituents will be explained as follows.

R¹ and R² may be mutually different and each represents a straight chain or branched alkyl group having from 1 to 10 carbon atoms. Particularly, a straight chain alkyl group having from 1 to 10 carbon atoms is preferable and a straight chain alkyl group having from 2 to 6 carbon atoms is more preferable. Preferably R¹ and R² are mutually different and more preferably R¹ and R² are the same alkyl groups. Specific preferable mode of R¹ and R² include one in which both R¹ and R² are an n-propyl group, an n-butyl group, an n-pentyl group, or an n-hexyl group or one in which R¹ is an ethyl group and R² is an n-butyl group.

(NR³R⁴)_(m) means that any one of the 6-position to the 9-position is substituted with m (NR³R⁴)s. m is an integer of 1 or 2. Either 1 or 2 is preferable, with 1 being more preferable. Regarding the position of substitution, when m is 1, the 7-position or the 9-position is preferable, with the 7-position being more preferable, and when m is 2, it is preferable that the two positions consisting of the 7-position and the 9-position are substituted with the same NR³R⁴. R³ and R⁴, which may be mutually different, each represents a straight chain or branched alkyl group having from 1 to 5 carbon atoms. In particular, a straight chain alkyl group having from 1 to 3 carbon atoms is preferable, a methyl group or an ethyl group is more preferable, and a methyl group is most preferable. Specific preferable modes of (NR³R⁴)_(m) include a 7-dimethylamino group, a 7-diethylamino group, a 7-ethylmethylamino group, a 9-dimethylamino group, and a 7,9-bis (dimethylamino) group.

Y represents any one of an —NHCS—, an —NHCSNH—, and an —NHCSO—. Here, —NH in the —NHCS— represents a bond that links with an adjacent benzene ring and CS— represents a bond that links with an adjacent Z, and —NH in —NHCSO— represents a bond that links with an adjacent benzene ring, and CSO— represents a bond that links with an adjacent Z. Regarding Y, —NHCS— or —NHCSNH— is preferable; the position of its substitution on the benzene ring is any one of an ortho-position, a meta-position, and a para-position, a meta- or para-position is preferable, and a meta-position is most preferable.

Z—(N⁺R⁵R⁶R⁷)_(n) is an alkyl group or alkenyl group having from 2 to 10 carbon atoms that is substituted with n (—N⁺R⁵R⁶R⁷)s and at least one of methylenes that constitute Z may be replaced by any one of a phenylene and an —O—; n is an integer of 1 or 2, both 1 and 2 are preferable, and 1 is more preferable.

Among the alkyl groups having 2 to 10 carbon atoms and alkenyl groups having from 2 to 10 carbon atoms and substituted with n (—N⁺R⁵R⁶R⁷)s, a straight chain or branched alkyl group having from 2 to 10 carbon atoms is preferable, and a straight chain alkyl group having from 2 to 10 carbon atoms or a branched alkyl group having from 3 to 7 carbon atoms is more preferable. When the alkyl group or the alkenyl group is substituted with one —N⁺R⁵R⁶R⁷, both the straight chain alkyl groups having from 2 to 10 carbon atoms and the branched alkyl group having from 3 to 7 carbon atoms are preferable and the straight chain alkyl group having from 2 to 10 carbon atoms is more preferable. When the alkyl group or the alkenyl group is substituted with two (—N⁺R⁵R⁶R⁷)s, a branched chain alkyl group having from 3 to 6 carbon atoms is preferable. In the case of the straight chain alkyl group having from 2 to 10 carbon atoms that is substituted with one —N⁺R⁵R⁶R⁷, it is particularly preferable that Z represents a straight chain methylene group having from 2 to 10 carbon atoms.

The at least one of methylenes that constitute Z may preferably be replaced by any one of a phenylene and an —O—; however, more preferably it is not at all replaced. On this occasion, a preferable mode of Z is as described above.

Even when the at least one of methylenes that constitute Z is replaced by any one of a phenylene and an —O—, a straight chain alkyl group having from 2 to 10 carbon atoms that is substituted with one —N⁺R⁵R⁶R⁷ is preferable, and it is particularly preferable that Z represents a straight chain methylene group having from 2 to 10 carbon atoms. A preferable mode of replacement is any one of replacement of one methylene by a phenylene, replacement of one methylene by an —O—, and replacement of one methylene by a phenylene and another methylene by an —O—. A more preferable mode of replacement is replacement of one methylene by a phenylene. However, the —O— by which one methylene is replaced referred to herein is different from the oxygen atom in the —NHCSO— represented by Y. The phenylene is any one of those represented by the following formulae (phe-1), (phe-2), and (phe-3), among which the formulae (phe-1) or (phe-2) is preferable, and the formula (phe-1) is more preferable.

Replacement of at least one of methylenes by a phenylene or an —O— is, for example, as illustrated in a figure below.

Specific preferable modes of Z include formulae from (sp-1) to (sp-23) below. In the formulae, *a is bonded to Y in the formula (1) and *b is bonded to N⁺R⁵R⁶R⁷. The formulae (sp-19) and (sp-20) are specific examples when n is 2 and the remaining formulae are specific examples when n is 1.

When Y represents —NHCS—, it is particularly preferable that Z is represented by any one of formulae from (sp-1) to (sp-10), from (sp-14) to (sp-16), (sp-18), (sp-19), (sp-21), and (sp-22); among these, the formulae from (sp-1) to (sp-9) are preferable. When Y represents —NHCSNH—, it is particularly preferable that Z is represented by any one of the formulae from (sp-1) to (sp-9), from (sp-12) to (sp-14), (sp-17), and (sp-20). Among them, the formulae (sp-1) to (sp-9) are more preferable. When Y represents —NHCSO—, it is particularly preferable that Z is any one of the formulae from (sp-1) to (sp-9) and (sp-11); among these, the formulae from (sp-1) to (sp-9) are more preferable.

N⁺R⁵R⁶R⁷ is any one of I), II), and III) below that are mutually independent.

I) R⁵, R⁶, and R⁷ may be mutually different and each represents an alkyl group, alkenyl group, or alkynyl group having from 1 to 10 carbon atoms. The alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, and further, at least one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—. R⁸ represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. R⁹ and R¹⁰, which may be mutually different, each represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. W⁻represents a counter anion.

When R⁵, R⁶, and R⁷ each represents an alkyl group, the alkyl group has preferably from 1 to 10 carbon atoms, any one of 1 to 10 is preferable as the number of carbon atoms(s) and more preferably the alkyl group is of a straight chain having from 1 to 10 carbon atoms. Specific preferable examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an i-butyl group, an n-pentyl group, an i-pentyl group, an n-hexyl group, a 3,3-dimethylbutyl group, an n-heptyl group, a 2,2-dimethylpentyl group, an n-octyl group, an n-nonyl group, an n-decanyl group, and a 2,3-diethylhexyl group. When R⁵, R⁶, and R⁷ each represents an alkenyl group, the alkenyl group has preferably from 3 to 8 carbon atoms, and more preferably the alkenyl group is of a straight chain having 3, 4, 5, 6, or 8 carbon atoms or of a branched one having 4, 6, or 7 carbon atoms. Specific preferable examples of the alkenyl group include a 2-propenyl group, a 2-methyl-2-propenyl group, a 3-butenyl group, a 4-pentenyl group, a 4-methyl-4-pentenyl group, a 5-hexenyl group, a 2-hexenyl group, a 5-methyl-5-hexenyl group, and a 2,7-octadienyl group. When R⁵, R⁶, and R⁷ represent an alkynyl group, the alkynyl group has preferably from 3 to 9 carbon atoms, and more preferably the alkynyl group is of a straight chain having 3, 5, 6, 7, or 9 carbon atoms or of a branched one having 6 carbon atoms. Specific preferable examples of the alkynyl group include a 2-propynyl group, a 2-pentynyl group, a 4-methyl-2-pentynyl group, a 2-hexynyl group, a 2-heptynyl group, and a 2-nonynyl group.

These preferable alkyl groups, alkenyl groups, and alkynyl groups, particularly alkyl groups, may be substituted with at least one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and a —SO₃H group. Further, at least one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly at least one of methylenes that constitute the alkyl group, may be replaced by any one of a phenylene, a thienylene, a furylene, an —O—, a —CO₂—, an —NHCO—, an —NR⁸— (where R⁸ represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms, preferably a straight chain alkyl group having from 1 to 3 carbon atoms or a straight chain alkenyl group having 3 carbon atoms, and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group), and an —N⁺W⁻R⁹R¹⁰— (where R⁹ and R¹⁰, which may be mutually different, each represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms, preferably a straight chain alkyl group having from 1 to 3 carbon atoms or a straight chain alkenyl group having 3 carbon atoms, and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group). It is more preferable that the alkenyl group and the alkynyl group are neither substituted nor replaced.

More preferable modes include any one of 1) a mode in which the preferable alkyl group, alkenyl group, and alkynyl group, in particular the alkyl group, represented by R⁵, R⁶, and R⁷ is substituted with any one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, 2) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with two hydroxyl groups, 3) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group and one —SO₃H group, 4) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one oxo group and one phenyl group, 5) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group and two phenyl groups, 6) a mode in which at least one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly at least one of methylenes that constitute the alkyl group is replaced by any one of a phenylene, a furylene, a —CO₂—, an —NHCO—, an —NR⁸— (where R⁸ represents any one of a straight chain alkyl group having from 1 to 3 carbon atoms, a straight chain alkenyl group having 3 carbon atoms, a straight chain alkyl group having from 1 to 3 carbon atoms that is substituted with one hydroxyl group, and a straight chain alkyl group having from 1 to 3 carbon atoms that is substituted with one phenyl group, with specific examples thereof including a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, and a benzyl group), and an —N⁺W⁻R⁹R¹⁰— (where R⁹ and R¹⁰ may be mutually different and each represents a straight chain alkyl group having from 1 to 3 carbon atoms, a straight chain alkenyl group having 3 carbon atoms, a straight chain alkyl group having from 1 to 3 carbon atoms that is substituted with one hydroxyl group, and a straight chain alkyl group having from 1 to 3 carbon atoms that is substituted with one phenyl group, with specific examples thereof including a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, and a benzyl group), 7) a mode in which two methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly two methylenes that constitute the alkyl group are replaced by any one of two (—O—)s, one phenylene and one —O—, one —O— and one —NR⁸—, and one —NHCO— and one —O—, 8) a mode in which three methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly three methylenes that constitute the alkyl group are replaced by two (—O—)s and one —NR⁸—, or one phenylene and two (—NHCO—)s, 9) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group, and further, one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes that constitute the alkyl group is replaced by an —O—, 10) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group, and further, one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes that constitute the alkyl group is replaced by an —NR⁸—, 11) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group, and further one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes that constitute the alkyl group is replaced by a furylene, 12) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one oxo group, and further, one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes that constitute the alkyl group is replaced by a thienylene, 13) a mode in which the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one oxo group, and further, two of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly two methylenes that constitute the alkyl group, are replaced by one —O— and one phenylene, or the preferable alkyl group, alkenyl group, and alkynyl group represented by R⁵, R⁶, and R⁷ are neither substituted nor replaced.

In the most preferable mode, R⁵, R⁶, and R⁷ each represents any one of a straight chain alkyl group having from 1 to 10 carbon atoms, a straight chain alkyl group having from 1 to 10 carbon atoms that is substituted with one phenyl group, a straight chain alkyl group having from 1 to 10 carbon atoms that is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 6 or 8 carbon atoms, a branched alkenyl group having 4, 6, or 7 carbon atoms, a straight chain alkynyl group having 3, 5, 6, 7, or 9 carbon atoms, and a branched alkynyl group having 6 carbon atoms.

II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring that is formed by 4 to 9 carbon atoms in addition to an ammonium nitrogen atom, provided that the position of its bonding with Z is at the ammonium nitrogen atom. In the monocyclic ring and the bicyclic ring, one of the carbon atoms that constitute the ring may be replaced by any one atom of oxygen, nitrogen, and sulfur, and further, the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a thioxo group, a cyano group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an —R¹¹. R¹¹ represents an alkyl group or alkenyl group having from 1 to 8 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and a —SO₃H group. Further, at least one of methylenes that constitute the alkyl and the alkenyl group, may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—. R⁸ represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. R⁹ and R¹⁰, which may be mutually different, each represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms, and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. W⁻ represents a counter anion. Among R⁵, R⁶, and R⁷, a group that is not involved in the formation of the monocyclic and the bicyclic ring represents an alkyl group, alkenyl group, or an alkynyl group having from 1 to 10 carbon atoms. The alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group. Further, at least one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a naphthylene, a thienylene, a furylene, a pyridylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an NR⁸, and an —N⁺W⁻R⁹R¹⁰—. R⁸ represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. R⁹ and R¹⁰ may be mutually different and each represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms, and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. W represents a counter anion.

The monocyclic ring or bicyclic ring represented by the N⁺R⁵R⁶R⁷ is preferably any one of a pyrrolidinium ring, a piperidinium ring, a morpholinium ring, a thiomorpholinium ring, a piperazinium ring, an azepanium ring, a quinuclidinium ring, and a 1,4-diazabicyclo[2.2.2]octanium ring. The monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂— group, and an —R¹¹. Here, R¹¹ is preferably an alkyl group having from 1 to 6 carbon atoms or an alkenyl group having 3 carbon atoms and more preferably a straight chain alkyl group having from 1 to 5 carbon atoms (for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, or an n-pentyl group), a branched alkyl group having 6 carbon atoms (for example, a 3,3-dimethylbutyl group), a straight chain alkenyl group having 3 carbon atoms (for example, a 2-propenyl group). The alkyl group may be substituted with at least one of a hydroxyl group, a cyano group, a phenyl group, and a —CONH₂ group. Further, at least one of methylenes that constitute the alkyl group may be replaced by any one of an —O—, a —CO₂—, and an —NHCO—. Among R⁵, R⁶, and R⁷, a group that is not involved in the formation of the ring, represents an alkyl group having from 1 to 6 carbon atoms (preferably a straight chain alkyl group having from 1 to 6 carbon atoms), an alkenyl group having from 3 to 4 carbon atoms (preferably a straight chain alkenyl group having from 3 to 4 carbon atoms), or an alkynyl group having from 3 to 6 carbon atoms (preferably a straight chain alkynyl group having 3, 4, or 6 carbon atoms). The alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group may be substituted with at least one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, an oxo group, a nitro group, a carboxyl group, and an —SO₃H group. Further, at least one of methylenes that constitute the alkyl group may be replaced by any one of a phenylene, an —O—, and a —CO₂—. It is more preferable that the alkenyl group and the alkynyl group are neither substituted nor replaced.

In a more preferable mode, the pyrrolidinium ring, the piperidinium ring, the morpholinium ring, the thiomorpholinium ring, the piperazinium ring, the azepanium ring, the quinuclidinium ring, and the 1,4-diazabicyclo[2.2.2]octanium ring are 1) substituted with any one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂ group, and an R¹¹ group, 2) substituted with one cyano group and one hydroxyl group, 3) substituted with one hydroxyl group and one R¹¹, 4) substituted with one oxo group and one R¹¹, 5) substituted with two oxo groups, or 6) substituted with two (R¹¹)s. Alternatively, the pyrrolidinium ring, the piperidinium ring, the morpholinium ring, the thiomorpholinium ring, the piperazinium ring, the azepanium ring, the quinuclidinium ring, and the 1,4-diazabicyclo[2.2.2]octanium ring are unsubstituted. Here, R¹¹ represents a straight chain alkyl group having from 1 to 5 carbon atoms (for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, or an n-pentyl group), a branched alkyl group having 6 carbon atoms (for example, a 3,3-dimethylbutyl group), or a straight chain alkenyl group having 3 carbon atoms (for example, a 2-propenyl group), in which 1) the alkyl group is substituted with one hydroxyl group or one phenyl group, 2) one of methylenes that constitute the alkyl group is replaced by either a —CO₂— or an —NHCO—, 3) two methylenes that constitute the alkyl group are replaced by one —O— and one —NHCO—, 4) the alkyl group is substituted with one cyano group and further, one of methylenes that constitute the alkyl group is replaced by an —O—, 5) the alkyl group is substituted with one —CONH₂ and further, one of methylenes that constitute the alkyl group is replaced by an —O—, 6) the alkyl group is substituted with one phenyl group and further, one of methylenes that constitute the alkyl group is replaced by a —CO₂—, 7) the alkyl group is substituted with one phenyl group and further, one of methylenes that constitute the alkyl group is replaced by an —NHCO—, or 8) the alkyl group is neither substituted nor replaced. Specific examples of R¹¹ include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a benzyl group, an acetylamino group, a t-butoxycarbonylamino group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-cyanoethoxy group, a (2-cyanoethoxy)methyl group, a 2-carbomoylethoxy group, an ethoxycarbonyl group, a t-butoxycarbonyl group, a benzoyloxy group, a phenylacetylamino group, a butanoylamino group, and a pentanoylamino group. Among R⁵, R⁶, and R⁷, a group that is not involved in the formation of the ring represents a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkenyl group having from 3 to 4 carbon atoms, or a straight chain alkynyl group having 3, 4, or 6 carbon atoms, in which 1) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with any one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, a carboxyl group, and an —SO₃H group, 2) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with two hydroxyl groups, 3) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one hydroxyl group and one —SO₃H, 4) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with four hydroxyl groups and one oxo group, 5) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one nitro group and one morpholyl group, 6) one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes that constitute the alkyl group is replaced by a —CO₂—, or 7) the alkyl group, the alkenyl group, and the alkynyl group, particularly the alkyl group is substituted with one morpholyl group and further, one of methylenes that constitute the alkyl group, the alkenyl group, and the alkynyl group, particularly one of methylenes that constitute the alkyl group is replaced by an —O—, or the alkyl group, the alkenyl group, and the alkynyl group are neither substituted nor replaced.

The most preferable mode is one in which the ring is a pyrrolidinium ring, a piperidinium ring, an azepanium ring, a quinuclidinium ring, or a 1,4-diazabicyclo[2.2.2] that is substituted with any one of a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a benzyl group, a hydroxyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group; or unsubstituted. Among R⁵, R⁶, and R⁷, a group that is not involved in the formation of the ring represents any one of a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkyl group having from 1 to 6 carbon atoms that is substituted with one phenyl group, a straight chain alkyl group that is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 4 carbon atoms, and a straight chain alkynyl group having 3, 4, or 6 carbon atoms.

Regarding the group that is not involved in the formation of the ring, specific preferable examples of the straight chain alkyl group having from 1 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group; specific preferable examples of the straight chain alkenyl group having from 3 to 4 carbon atoms include a 2-propenyl group, a 3-butenyl group, and a 2,7-octadienyl group; and specific preferable examples of the straight chain alkynyl group having 3, 4, or 6 carbon atoms include a 2-propynyl group, a 2-butynyl group, and a 2,4-hexadiynyl group.

III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring. Here, the position of bonding with Z is at the ammonium nitrogen atom. The pyridinium ring, the quinolinium ring, and the isoquinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, an alkoxy group having from 1 to 5 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an —R¹² group. R¹² represents an alkyl group or alkenyl group having from 1 to 9 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, an hydroxyl group, an oxo group, thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group. Further, at least one of methylenes that constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—. R⁸ represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms. The alkyl group and the alkenyl group may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. R⁹ and R¹⁰ are mutually different and each represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms, and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group. W^(—) represents a counter anion.

It is preferable that among the pyridinium ring, the quinolinium ring, and the isoquinolinium ring, the pyridinium ring and the quinolinium ring, particularly the pyridinium ring, is substituted with at least one of a cyano group, a nitro group, a phenyl group, a thienyl group, a pyridyl group, an alkoxy group having from 1 to 3 carbon atoms, a carboxyl group, a —CONH²— group, and an —R¹² group. Here, R¹² represents an alkyl group having from 1 to 9 carbon atoms (preferably a straight chain alkyl group having from 1 to 7 carbon atoms, or a branched alkyl group having from 3 to 5 or 9 carbon atoms) or an alkenyl group having from 2 to 4 carbon atoms (preferably a straight chain alkenyl group having from 2 to 4 carbon atoms). The alkyl group and the alkenyl group, particularly the alkyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a cyano group, a nitro group, a hydroxyl group, an oxo group, a carboxyl group, and an —SO₃H group and further, at least one of methylenes that constitute the alkyl group and the alkenyl group, particularly one of methylenes that constitute the alkyl group may be replaced by any one of an —S—, a —CO₂—, an —NHCO—, and an —NR⁸—, where R⁸ represents an alkyl group having from 1 to 3 carbon atoms (preferably a straight chain alkyl group having from 1 to 3 carbon atoms) and the alkyl group may be substituted with at least one (preferably one) hydroxyl group.

In a more preferable mode, the ring is any one of 1) a pyridinium ring substituted with any one of a cyano group, a phenyl group, a thienyl group, a pyridyl group, a methoxy group, an ethoxy group, a propoxy group, a carboxyl group, a —CONH₂— group, and an —R¹² group, 2) a pyridinium ring substituted with two cyano groups, 3) a pyridinium ring substituted with two (—R¹²)s, 4) a pyridinium ring substituted with one cyano group and one —R¹², 5) a pyridinium ring substituted with one phenyl group and one —R¹², 6) a quinolinium ring substituted with any one of a cyano group, a nitro group, a carboxyl group, a methoxy group, an ethoxy group, a propoxy group, and an —R¹² group, 7) a quinolinium ring substituted with one methoxy group and one —R¹², 8) a quinolinium ring substituted with one nitro group and one —R², 9) an unsubstituted pyridinium ring, 10) an unsubstituted quinolinium ring, and 11) an unsubstituted isoquinolinium ring. Here, R¹² represents a straight chain alkyl group having from 1 to 7 carbon atoms (for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, or an n-heptyl group), a branched alkyl group having from 3 to 5 or 9 carbon atoms (for example, an i-propyl group, a t-butyl group, a 3-pentyl group, or a 5-nonyl group) or a straight chain alkenyl group having 2 to 4 carbon atoms (for example, a vinyl group or a 3-butenyl group), and 1) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with any one of a phenyl group, a naphthyl group, a pyridyl group, a cyano group, a nitro group, a hydroxyl group, an oxo group, a carboxyl group, and an —SO₃H group, 2) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one oxo group and one phenyl group, 3) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with two hydroxyl groups and one one pyridyl group, 4) one of methylenes that constitute the alkyl group and the alkenyl group, particularly one of methylenes that constitute the alkyl group is replaced by a —CO₂—, 5) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one hydroxyl group and further, one of methylenes that constitute the alkyl group and the alkenyl group, particularly one of methylenes that constitute the alkyl group is replaced by an —NHCO—, 6) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one oxo group, and further, one of methylenes that constitute the alkyl group and the alkenyl group, particularly one of methylenes that constitute the alkyl group is replaced by a —CO₂—, 7) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one phenyl group, and further, one of methylenes that constitute the alkyl group and the alkenyl group, particularly one of methylenes that constitute the alkyl group is replaced by a —CO₂—, 8) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one carboxyl group, and further, one of methylenes that constitute the alkyl group and the alkenyl group, particularly one of methylenes that constitute the alkyl group is replaced by an —S—, 9) the alkyl group and the alkenyl group, particularly the alkyl group is substituted with one hydroxyl group and one oxo group, and further, one of methylenes that constitute the alkyl group and the alkenyl group, particularly one of methylenes that constitute the alkyl group is replaced by an —NR⁸— (where R⁸ represents a methyl group, an ethyl group, an n-propyl group, a 2-hydroxyethyl group, or a 3-hydroxypropyl group), or 10) the alkyl group and the alkenyl group are neither substituted nor replaced. Specific examples of R¹² include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a 3-pentyl group, a 5-nonyl group, a vinyl group, a benzyl group, a 3-phenylpropyl group, a 2-(1-naphthyl)vinyl group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a formyl group, an acetyl group, a propionyl group, a benzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, a hexoxycarbonyl group, a benzyloxycarbonyl group, a 2-propenyloxycarbonyl group, an ethoxycarbonylmethyl group, a 2-(methoxycarbonyl)ethyl group, an ethoxycarbonylmethylcarbonyl group, a 2-hydroxyethylaminocarbonyl group, a bis(2-hydroxyethyl)aminocarbonyl group, a 2-carboxyvinyl group, a carboxymethylthio group, a cyanomethyl group, a 2-nitrovinyl group, a 2-(4-pyridyl)ethyl group, a 2-(4-pyridyl)vinyl group, a 3-(4-pyridyl)propyl group, a 2-(4-pyridyl)-1,2-dihydroxyethyl group, and a 2-sulfoethyl group.

The most preferable mode, the ring is any one of an unsubstituted pyridinium ring, an unsubstituted quinolinium ring, an unsubstituted isoquinolinium ring, a pyridinium ring substituted with any one of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a vinyl group, a phenyl group, a benzyl group, a 3-phenylpropyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group, a pyridinium ring substituted with either two methyl groups or two ethyl groups, a pyridinium ring substituted with one phenyl group and one methyl group, and a quinolinium ring substituted with either one methyl group or one i-propyl group.

Examples of the naphthyl used in the explanation from I) to III) above include 1-naphthyl and 2-naphthyl, with 1-naphthyl being preferable. Examples of the pyridyl include 1-pyridyl, 2-pyridyl, 3-pyridyl, and 4-pyridyl, preferably 1-pyridyl and 4-pyridyl, and more preferably 4-pyridyl. Examples of the quinolyl include 1-quinolyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, and 8-quinolyl, preferably 1-quinolyl and 4-quinolyl. Examples of the thienyl include 2-thienyl and 3-thienyl, preferably 2-thienyl. Examples of the furyl include 2-furyl, and 3-furyl, preferably 2-furyl. Examples of the piperidyl include 1-piperidyl, 2-piperidyl, 3-piperidyl, and 4-piperidyl, preferably 1-piperidyl and 4-piperidyl, and more preferably 1-piperidyl. Examples of the pyrrolidyl include 1-pyrrolidyl, 2-pyrrolidyl, and 3-pyrrolidyl, preferably 1-pyrrolidyl. Examples of the morpholyl include 2-morpholyl, 3-morpholyl, and 4-morpholyl, particularly preferably 4-morpholyl. Preferable examples of the cycloalkyl having from 3 to 7 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. The phenylene is any one of the formulae (phe-1) to (phe-3) mentioned earlier and preferably the formula (phe-1) or (phe-2), and more preferably the formula (phe-1). The thienylene is any one of the formulae (thi-1) to (thi-4) below, with the formula (thi-1) being particularly preferable.

The furylene is any one of the formulae (fur-1) to (fur-4) below, with formula (fur-1) being particularly preferable.

The cyclohexylene is any one of the formulae (hex-1) to (hex-3) below, preferably the formula (hex-1) or the formula (hex-2), and more preferably the formula (hex-1). The cyclopentylene is any one of the formulae (pen-1) and (pen-2) below, preferably the formula (pen-1).

Specific examples of the —N⁺R⁵R⁶R⁷ that correspond to I) include the formulae (an-1) to (an-158) below.

Specific examples of the —N⁺R⁵R⁶R⁷ that correspond to II) include the formulae (an-159) to (an-299) below.

Specific examples of the —N⁺R⁵R⁶R⁷ that correspond to III) include formulae from (an-300) to (an-377) below.

W⁻ and X⁻ each represents a counter anion which may be negatively charged ions regardless of their valence and can electrically neutralize a positively charged ammonium ion in the compound of the present invention, and it is preferable that they are pharmaceutically acceptable anions. Examples of preferable anion include F⁻, Cl⁻, Br⁻, I⁻, OH⁻, CH₃SO₃ ⁻, CF₃SO₃ ⁻, HCO₂ ⁻, CH₃CO₂ ⁻, CF₃CO₂ ⁻, ClO₄ ⁻, IO₄ ⁻, HCO₃ ⁻, CO₃ ²⁻, NO₃ ⁻, HSO₄ ⁻, SO₄ ²⁻, H₂PO₄ ⁻, HPO₄ ²⁻, and PO₄ ³⁻, among which Cl⁻ and Br⁻ are particularly preferable. W⁻ and X⁻ may be mutually different but more preferably they are the same.

In the compounds of the present invention, asymmetric centers can exist also in Z and (N⁺R⁵R⁶R⁷) in addition to the 3-position and the 5-position in the formula (1), so that there can be a plurality of stereo isomers depending on the number of asymmetric centers. Not only pure stereoisomers but also mixtures of any plural number of isomers are included in the scope of the present invention. Further, there can exist a plurality of geometrical isomers depending on the types of Z and (N⁺R⁵R⁶R⁷) in the compounds of the present invention. Not only pure geometrical isomers but also mixtures of any plural number of the isomers are included in the scope of the present invention.

Further, the present invention provides pharmaceutical compositions containing the compounds of the present invention as active ingredients; a pharmaceutical composition that is a cholesterol lowering agent, a pharmaceutical composition that is a therapeutic or preventive agent for any one of hyperlipidemia, arteriosclerosis, and syndrome X, a pharmaceutical composition that is a treating or preventing agent for cholestasis-accompanying hepatopathy, a pharmaceutical composition that is a treating or preventing agent for any one of primary biliary cirrhosis and primary sclerosing cholangitis, or a pharmaceutical composition that is a treating or preventing agent for obesity and fatty liver.

[Embodiments of the Invention]

Specific examples of the compound represented by formula (1) include the following compounds and acid addition salts thereof.

Compounds in which both R¹ and R² are butyl groups, NR³R⁴ is a 7-dimethylamino group, X⁻ is Br⁻, and the bonding position of Y is the meta-position include those compounds mentioned in Table 1 (from 1A001 to 1A6409, from 1U001 to 1U5278, and from 1C001 to 1C3770). From (sp-1) to (sp-22) and from (an-1) to (an-377) in Table 1, are as mentioned earlier. TABLE 1 Y = NHCS Y = NHCSO Exempli- Exempli- fication Y = NHCSNH fication No Z N⁺R⁵R⁶R⁷

No Z N⁺R⁵R⁶R⁷ No Z N⁺R⁵R⁶R⁷ 1A0001 sp-1 an-1 1U0001 sp-1 an-1 1C0001 sp-1 an-1 1A0002 sp-1 an-2 1U0002 sp-1 an-2 1C0002 sp-1 an-2 1A0003 sp-1 an-3 1U0003 sp-1 an-3 1C0003 sp-1 an-3 1A0004 sp-1 an-4 1U0004 sp-1 an-4 1C0004 sp-1 an-4 1A0005 sp-1 an-5 1U0005 sp-1 an-5 1C0005 sp-1 an-5 1A0006 sp-1 an-6 1U0006 sp-1 an-6 1C0006 sp-1 an-6 1A0007 sp-1 an-7 1U0007 sp-1 an-7 1C0007 sp-1 an-7 1A0008 sp-1 an-8 1U0008 sp-1 an-8 1C0008 sp-1 an-8 1A0009 sp-1 an-9 1U0009 sp-1 an-9 1C0009 sp-1 an-9 1A0010 sp-1 an-10 1U0010 sp-1 an-10 1C0010 sp-1 an-10 1A0011 sp-1 an-11 1U0011 sp-1 an-11 1C0011 sp-1 an-11 1A0012 sp-1 an-12 1U0012 sp-1 an-12 1C0012 sp-1 an-12 1A0013 sp-1 an-13 1U0013 sp-1 an-13 1C0013 sp-1 an-13 1A0014 sp-1 an-14 1U0014 sp-1 an-14 1C0014 sp-1 an-14 1A0015 sp-1 an-15 1U0015 sp-1 an-15 1C0015 sp-1 an-15 1A0016 sp-1 an-16 1U0016 sp-1 an-16 1C0016 sp-1 an-16 1A0017 sp-1 an-17 1U0017 sp-1 an-17 1C0017 sp-1 an-17 1A0018 sp-1 an-18 1U0018 sp-1 an-18 1C0018 sp-1 an-18 1A0019 sp-1 an-19 1U0019 sp-1 an-19 1C0019 sp-1 an-19 1A0020 sp-1 an-20 1U0020 sp-1 an-20 1C0020 sp-1 an-20 1A0021 sp-1 an-21 1U0021 sp-1 an-21 1C0021 sp-1 an-21 1A0022 sp-1 an-22 1U0022 sp-1 an-22 1C0022 sp-1 an-22 1A0023 sp-1 an-23 1U0023 sp-1 an-23 1C0023 sp-1 an-23 1A0024 sp-1 an-24 1U0024 sp-1 an-24 1C0024 sp-1 an-24 1A0025 sp-1 an-25 1U0025 sp-1 an-25 1C0025 sp-1 an-25 1A0026 sp-1 an-26 1U0026 sp-1 an-26 1C0026 sp-1 an-26 1A0027 sp-1 an-27 1U0027 sp-1 an-27 1C0027 sp-1 an-27 1A0028 sp-1 an-28 1U0028 sp-1 an-28 1C0028 sp-1 an-28 1A0029 sp-1 an-29 1U0029 sp-1 an-29 1C0029 sp-1 an-29 1A0030 sp-1 an-30 1U0030 sp-1 an-30 1C0030 sp-1 an-30 1A0031 sp-1 an-31 1U0031 sp-1 an-31 1C0031 sp-1 an-31 1A0032 sp-1 an-32 1U0032 sp-1 an-32 1C0032 sp-1 an-32 1A0033 sp-1 an-33 1U0033 sp-1 an-33 1C0033 sp-1 an-33 1A0034 sp-1 an-34 1U0034 sp-1 an-34 1C0034 sp-1 an-34 1A0035 sp-1 an-35 1U0035 sp-1 an-35 1C0035 sp-1 an-35 1A0036 sp-1 an-36 1U0036 sp-1 an-36 1C0036 sp-1 an-36 1A0037 sp-1 an-37 1U0037 sp-1 an-37 1C0037 sp-1 an-37 1A0038 sp-1 an-38 1U0038 sp-1 an-38 1C0038 sp-1 an-38 1A0039 sp-1 an-39 1U0039 sp-1 an-39 1C0039 sp-1 an-39 1A0040 sp-1 an-40 1U0040 sp-1 an-40 1C0040 sp-1 an-40 1A0041 sp-1 an-41 1U0041 sp-1 an-41 1C0041 sp-1 an-41 1A0042 sp-1 an-42 1U0042 sp-1 an-42 1C0042 sp-1 an-42 1A0043 sp-1 an-43 1U0043 sp-1 an-43 1C0043 sp-1 an-43 1A0044 sp-1 an-44 1U0044 sp-1 an-44 1C0044 sp-1 an-44 1A0045 sp-1 an-45 1U0045 sp-1 an-45 1C0045 sp-1 an-45 1A0046 sp-1 an-46 1U0046 sp-1 an-46 1C0046 sp-1 an-46 1A0047 sp-1 an-47 1U0047 sp-1 an-47 1C0047 sp-1 an-47 1A0048 sp-1 an-48 1U0048 sp-1 an-48 1C0048 sp-1 an-48 1A0049 sp-1 an-49 1U0049 sp-1 an-49 1C0049 sp-1 an-49 1A0050 sp-1 an-50 1U0050 sp-1 an-50 1C0050 sp-1 an-50 1A0051 sp-1 an-51 1U0051 sp-1 an-51 1C0051 sp-1 an-51 1A0052 sp-1 an-52 1U0052 sp-1 an-52 1C0052 sp-1 an-52 1A0053 sp-1 an-53 1U0053 sp-1 an-53 1C0053 sp-1 an-53 1A0054 sp-1 an-54 1U0054 sp-1 an-54 1C0054 sp-1 an-54 1A0055 sp-1 an-55 1U0055 sp-1 an-55 1C0055 sp-1 an-55 1A0056 sp-1 an-56 1U0056 sp-1 an-56 1C0056 sp-1 an-56 1A0057 sp-1 an-57 1U0057 sp-1 an-57 1C0057 sp-1 an-57 1A0058 sp-1 an-58 1U0058 sp-1 an-58 1C0058 sp-1 an-58 1A0059 sp-1 an-59 1U0059 sp-1 an-59 1C0059 sp-1 an-59 1A0060 sp-1 an-60 1U0060 sp-1 an-60 1C0060 sp-1 an-60 1A0061 sp-1 an-61 1U0061 sp-1 an-61 1C0061 sp-1 an-61 1A0062 sp-1 an-62 1U0062 sp-1 an-62 1C0062 sp-1 an-62 1A0063 sp-1 an-63 1U0063 sp-1 an-63 1C0063 sp-1 an-63 1A0064 sp-1 an-64 1U0064 sp-1 an-64 1C0064 sp-1 an-64 1A0065 sp-1 an-65 1U0065 sp-1 an-65 1C0065 sp-1 an-65 1A0066 sp-1 an-66 1U0066 sp-1 an-66 1C0066 sp-1 an-66 1A0067 sp-1 an-67 1U0067 sp-1 an-67 1C0067 sp-1 an-67 1A0068 sp-1 an-68 1U0068 sp-1 an-68 1C0068 sp-1 an-68 1A0069 sp-1 an-69 1U0069 sp-1 an-69 1C0069 sp-1 an-69 1A0070 sp-1 an-70 1U0070 sp-1 an-70 1C0070 sp-1 an-70 1A0071 sp-1 an-71 1U0071 sp-1 an-71 1C0071 sp-1 an-71 1A0072 sp-1 an-72 1U0072 sp-1 an-72 1C0072 sp-1 an-72 1A0073 sp-1 an-73 1U0073 sp-1 an-73 1C0073 sp-1 an-73 1A0074 sp-1 an-74 1U0074 sp-1 an-74 1C0074 sp-1 an-74 1A0075 sp-1 an-75 1U0075 sp-1 an-75 1C0075 sp-1 an-75 1A0076 sp-1 an-76 1U0076 sp-1 an-76 1C0076 sp-1 an-76 1A0077 sp-1 an-77 1U0077 sp-1 an-77 1C0077 sp-1 an-77 1A0078 sp-1 an-78 1U0078 sp-1 an-78 1C0078 sp-1 an-78 1A0079 sp-1 an-79 1U0079 sp-1 an-79 1C0079 sp-1 an-79 1A0080 sp-1 an-80 1U0080 sp-1 an-80 1C0080 sp-1 an-80 1A0081 sp-1 an-81 1U0081 sp-1 an-81 1C0081 sp-1 an-81 1A0082 sp-1 an-82 1U0082 sp-1 an-82 1C0082 sp-1 an-82 1A0083 sp-1 an-83 1U0083 sp-1 an-83 1C0083 sp-1 an-83 1A0084 sp-1 an-84 1U0084 sp-1 an-84 1C0084 sp-1 an-84 1A0085 sp-1 an-85 1U0085 sp-1 an-85 1C0085 sp-1 an-85 1A0086 sp-1 an-86 1U0086 sp-1 an-86 1C0086 sp-1 an-86 1A0087 sp-1 an-87 1U0087 sp-1 an-87 1C0087 sp-1 an-87 1A0088 sp-1 an-88 1U0088 sp-1 an-88 1C0088 sp-1 an-88 1A0089 sp-1 an-89 1U0089 sp-1 an-89 1C0089 sp-1 an-89 1A0090 sp-1 an-90 1U0090 sp-1 an-90 1C0090 sp-1 an-90 1A0091 sp-1 an-91 1U0091 sp-1 an-91 1C0091 sp-1 an-91 1A0092 sp-1 an-92 1U0092 sp-1 an-92 1C0092 sp-1 an-92 1A0093 sp-1 an-93 1U0093 sp-1 an-93 1C0093 sp-1 an-93 1A0094 sp-1 an-94 1U0094 sp-1 an-94 1C0094 sp-1 an-94 1A0095 sp-1 an-95 1U0095 sp-1 an-95 1C0095 sp-1 an-95 1A0096 sp-1 an-96 1U0096 sp-1 an-96 1C0096 sp-1 an-96 1A0097 sp-1 an-97 1U0097 sp-1 an-97 1C0097 sp-1 an-97 1A0098 sp-1 an-98 1U0098 sp-1 an-98 1C0098 sp-1 an-98 1A0099 sp-1 an-99 1U0099 sp-1 an-99 1C0099 sp-1 an-99 1A0100 sp-1 an-100 1U0100 sp-1 an-100 1C0100 sp-1 an-100 1A0101 sp-1 an-101 1U0101 sp-1 an-101 1C0101 sp-1 an-101 1A0102 sp-1 an-102 1U0102 sp-1 an-102 1C0102 sp-1 an-102 1A0103 sp-1 an-103 1U0103 sp-1 an-103 1C0103 sp-1 an-103 1A0104 sp-1 an-104 1U0104 sp-1 an-104 1C0104 sp-1 an-104 1A0105 sp-1 an-105 1U0105 sp-1 an-105 1C0105 sp-1 an-105 1A0106 sp-1 an-106 1U0106 sp-1 an-106 1C0106 sp-1 an-106 1A0107 sp-1 an-107 1U0107 sp-1 an-107 1C0107 sp-1 an-107 1A0108 sp-1 an-108 1U0108 sp-1 an-108 1C0108 sp-1 an-108 1A0109 sp-1 an-109 1U0109 sp-1 an-109 1C0109 sp-1 an-109 1A0110 sp-1 an-110 1U0110 sp-1 an-110 1C0110 sp-1 an-110 1A0111 sp-1 an-111 1U0111 sp-1 an-111 1C0111 sp-1 an-111 1A0112 sp-1 an-112 1U0112 sp-1 an-112 1C0112 sp-1 an-112 1A0113 sp-1 an-113 1U0113 sp-1 an-113 1C0113 sp-1 an-113 1A0114 sp-1 an-114 1U0114 sp-1 an-114 1C0114 sp-1 an-114 1A0115 sp-1 an-115 1U0115 sp-1 an-115 1C0115 sp-1 an-115 1A0116 sp-1 an-116 1U0116 sp-1 an-116 1C0116 sp-1 an-116 1A0117 sp-1 an-117 1U0117 sp-1 an-117 1C0117 sp-1 an-117 1A0118 sp-1 an-118 1U0118 sp-1 an-118 1C0118 sp-1 an-118 1A0119 sp-1 an-119 1U0119 sp-1 an-119 1C0119 sp-1 an-119 1A0120 sp-1 an-120 1U0120 sp-1 an-120 1C0120 sp-1 an-120 1A0121 sp-1 an-121 1U0121 sp-1 an-121 1C0121 sp-1 an-121 1A0122 sp-1 an-122 1U0122 sp-1 an-122 1C0122 sp-1 an-122 1A0123 sp-1 an-123 1U0123 sp-1 an-123 1C0123 sp-1 an-123 1A0124 sp-1 an-124 1U0124 sp-1 an-124 1C0124 sp-1 an-124 1A0125 sp-1 an-125 1U0125 sp-1 an-125 1C0125 sp-1 an-125 1A0126 sp-1 an-126 1U0126 sp-1 an-126 1C0126 sp-1 an-126 1A0127 sp-1 an-127 1U0127 sp-1 an-127 1C0127 sp-1 an-127 1A0128 sp-1 an-128 1U0128 sp-1 an-128 1C0128 sp-1 an-128 1A0129 sp-1 an-129 1U0129 sp-1 an-129 1C0129 sp-1 an-129 1A0130 sp-1 an-130 1U0130 sp-1 an-130 1C0130 sp-1 an-130 1A0131 sp-1 an-131 1U0131 sp-1 an-131 1C0131 sp-1 an-131 1A0132 sp-1 an-132 1U0132 sp-1 an-132 1C0132 sp-1 an-132 1A0133 sp-1 an-133 1U0133 sp-1 an-133 1C0133 sp-1 an-133 1A0134 sp-1 an-134 1U0134 sp-1 an-134 1C0134 sp-1 an-134 1A0135 sp-1 an-135 1U0135 sp-1 an-135 1C0135 sp-1 an-135 1A0136 sp-1 an-136 1U0136 sp-1 an-136 1C0136 sp-1 an-136 1A0137 sp-1 an-137 1U0137 sp-1 an-137 1C0137 sp-1 an-137 1A0138 sp-1 an-138 1U0138 sp-1 an-138 1C0138 sp-1 an-138 1A0139 sp-1 an-139 1U0139 sp-1 an-139 1C0139 sp-1 an-139 1A0140 sp-1 an-140 1U0140 sp-1 an-140 1C0140 sp-1 an-140 1A0141 sp-1 an-141 1U0141 sp-1 an-141 1C0141 sp-1 an-141 1A0142 sp-1 an-142 1U0142 sp-1 an-142 1C0142 sp-1 an-142 1A0143 sp-1 an-143 1U0143 sp-1 an-143 1C0143 sp-1 an-143 1A0144 sp-1 an-144 1U0144 sp-1 an-144 1C0144 sp-1 an-144 1A0145 sp-1 an-145 1U0145 sp-1 an-145 1C0145 sp-1 an-145 1A0146 sp-1 an-146 1U0146 sp-1 an-146 1C0146 sp-1 an-146 1A0147 sp-1 an-147 1U0147 sp-1 an-147 1C0147 sp-1 an-147 1A0148 sp-1 an-148 1U0148 sp-1 an-148 1C0148 sp-1 an-148 1A0149 sp-1 an-149 1U0149 sp-1 an-149 1C0149 sp-1 an-149 1A0150 sp-1 an-150 1U0150 sp-1 an-150 1C0150 sp-1 an-150 1A0151 sp-1 an-151 1U0151 sp-1 an-151 1C0151 sp-1 an-151 1A0152 sp-1 an-152 1U0152 sp-1 an-152 1C0152 sp-1 an-152 1A0153 sp-1 an-153 1U0153 sp-1 an-153 1C0153 sp-1 an-153 1A0154 sp-1 an-154 1U0154 sp-1 an-154 1C0154 sp-1 an-154 1A0155 sp-1 an-155 1U0155 sp-1 an-155 1C0155 sp-1 an-155 1A0156 sp-1 an-156 1U0156 sp-1 an-156 1C0156 sp-1 an-156 1A0157 sp-1 an-157 1U0157 sp-1 an-157 1C0157 sp-1 an-157 1A0158 sp-1 an-158 1U0158 sp-1 an-158 1C0158 sp-1 an-158 1A0159 sp-1 an-159 1U0159 sp-1 an-159 1C0159 sp-1 an-159 1A0160 sp-1 an-160 1U0160 sp-1 an-160 1C0160 sp-1 an-160 1A0161 sp-1 an-161 1U0161 sp-1 an-161 1C0161 sp-1 an-161 1A0162 sp-1 an-162 1U0162 sp-1 an-162 1C0162 sp-1 an-162 1A0163 sp-1 an-163 1U0163 sp-1 an-163 1C0163 sp-1 an-163 1A0164 sp-1 an-164 1U0164 sp-1 an-164 1C0164 sp-1 an-164 1A0165 sp-1 an-165 1U0165 sp-1 an-165 1C0165 sp-1 an-165 1A0166 sp-1 an-166 1U0166 sp-1 an-166 1C0166 sp-1 an-166 1A0167 sp-1 an-167 1U0167 sp-1 an-167 1C0167 sp-1 an-167 1A0168 sp-1 an-168 1U0168 sp-1 an-168 1C0168 sp-1 an-168 1A0169 sp-1 an-169 1U0169 sp-1 an-169 1C0169 sp-1 an-169 1A0170 sp-1 an-170 1U0170 sp-1 an-170 1C0170 sp-1 an-170 1A0171 sp-1 an-171 1U0171 sp-1 an-171 1C0171 sp-1 an-171 1A0172 sp-1 an-172 1U0172 sp-1 an-172 1C0172 sp-1 an-172 1A0173 sp-1 an-173 1U0173 sp-1 an-173 1C0173 sp-1 an-173 1A0174 sp-1 an-174 1U0174 sp-1 an-174 1C0174 sp-1 an-174 1A0175 sp-1 an-175 1U0175 sp-1 an-175 1C0175 sp-1 an-175 1A0176 sp-1 an-176 1U0176 sp-1 an-176 1C0176 sp-1 an-176 1A0177 sp-1 an-177 1U0177 sp-1 an-177 1C0177 sp-1 an-177 1A0178 sp-1 an-178 1U0178 sp-1 an-178 1C0178 sp-1 an-178 1A0179 sp-1 an-179 1U0179 sp-1 an-179 1C0179 sp-1 an-179 1A0180 sp-1 an-180 1U0180 sp-1 an-180 1C0180 sp-1 an-180 1A0181 sp-1 an-181 1U0181 sp-1 an-181 1C0181 sp-1 an-181 1A0182 sp-1 an-182 1U0182 sp-1 an-182 1C0182 sp-1 an-182 1A0183 sp-1 an-183 1U0183 sp-1 an-183 1C0183 sp-1 an-183 1A0184 sp-1 an-184 1U0184 sp-1 an-184 1C0184 sp-1 an-184 1A0185 sp-1 an-185 1U0185 sp-1 an-185 1C0185 sp-1 an-185 1A0186 sp-1 an-186 1U0186 sp-1 an-186 1C0186 sp-1 an-186 1A0187 sp-1 an-187 1U0187 sp-1 an-187 1C0187 sp-1 an-187 1A0188 sp-1 an-188 1U0188 sp-1 an-188 1C0188 sp-1 an-188 1A0189 sp-1 an-189 1U0189 sp-1 an-189 1C0189 sp-1 an-189 1A0190 sp-1 an-190 1U0190 sp-1 an-190 1C0190 sp-1 an-190 1A0191 sp-1 an-191 1U0191 sp-1 an-191 1C0191 sp-1 an-191 1A0192 sp-1 an-192 1U0192 sp-1 an-192 1C0192 sp-1 an-192 1A0193 sp-1 an-193 1U0193 sp-1 an-193 1C0193 sp-1 an-193 1A0194 sp-1 an-194 1U0194 sp-1 an-194 1C0194 sp-1 an-194 1A0195 sp-1 an-195 1U0195 sp-1 an-195 1C0195 sp-1 an-195 1A0196 sp-1 an-196 1U0196 sp-1 an-196 1C0196 sp-1 an-196 1A0197 sp-1 an-197 1U0197 sp-1 an-197 1C0197 sp-1 an-197 1A0198 sp-1 an-198 1U0198 sp-1 an-198 1C0198 sp-1 an-198 1A0199 sp-1 an-199 1U0199 sp-1 an-199 1C0199 sp-1 an-199 1A0200 sp-1 an-200 1U0200 sp-1 an-200 1C0200 sp-1 an-200 1A0201 sp-1 an-201 1U0201 sp-1 an-201 1C0201 sp-1 an-201 1A0202 sp-1 an-202 1U0202 sp-1 an-202 1C0202 sp-1 an-202 1A0203 sp-1 an-203 1U0203 sp-1 an-203 1C0203 sp-1 an-203 1A0204 sp-1 an-204 1U0204 sp-1 an-204 1C0204 sp-1 an-204 1A0205 sp-1 an-205 1U0205 sp-1 an-205 1C0205 sp-1 an-205 1A0206 sp-1 an-206 1U0206 sp-1 an-206 1C0206 sp-1 an-206 1A0207 sp-1 an-207 1U0207 sp-1 an-207 1C0207 sp-1 an-207 1A0208 sp-1 an-208 1U0208 sp-1 an-208 1C0208 sp-1 an-208 1A0209 sp-1 an-209 1U0209 sp-1 an-209 1C0209 sp-1 an-209 1A0210 sp-1 an-210 1U0210 sp-1 an-210 1C0210 sp-1 an-210 1A0211 sp-1 an-211 1U0211 sp-1 an-211 1C0211 sp-1 an-211 1A0212 sp-1 an-212 1U0212 sp-1 an-212 1C0212 sp-1 an-212 1A0213 sp-1 an-213 1U0213 sp-1 an-213 1C0213 sp-1 an-213 1A0214 sp-1 an-214 1U0214 sp-1 an-214 1C0214 sp-1 an-214 1A0215 sp-1 an-215 1U0215 sp-1 an-215 1C0215 sp-1 an-215 1A0216 sp-1 an-216 1U0216 sp-1 an-216 1C0216 sp-1 an-216 1A0217 sp-1 an-217 1U0217 sp-1 an-217 1C0217 sp-1 an-217 1A0218 sp-1 an-218 1U0218 sp-1 an-218 1C0218 sp-1 an-218 1A0219 sp-1 an-219 1U0219 sp-1 an-219 1C0219 sp-1 an-219 1A0220 sp-1 an-220 1U0220 sp-1 an-220 1C0220 sp-1 an-220 1A0221 sp-1 an-221 1U0221 sp-1 an-221 1C0221 sp-1 an-221 1A0222 sp-1 an-222 1U0222 sp-1 an-222 1C0222 sp-1 an-222 1A0223 sp-1 an-223 1U0223 sp-1 an-223 1C0223 sp-1 an-223 1A0224 sp-1 an-224 1U0224 sp-1 an-224 1C0224 sp-1 an-224 1A0225 sp-1 an-225 1U0225 sp-1 an-225 1C0225 sp-1 an-225 1A0226 sp-1 an-226 1U0226 sp-1 an-226 1C0226 sp-1 an-226 1A0227 sp-1 an-227 1U0227 sp-1 an-227 1C0227 sp-1 an-227 1A0228 sp-1 an-228 1U0228 sp-1 an-228 1C0228 sp-1 an-228 1A0229 sp-1 an-229 1U0229 sp-1 an-229 1C0229 sp-1 an-229 1A0230 sp-1 an-230 1U0230 sp-1 an-230 1C0230 sp-1 an-230 1A0231 sp-1 an-231 1U0231 sp-1 an-231 1C0231 sp-1 an-231 1A0232 sp-1 an-232 1U0232 sp-1 an-232 1C0232 sp-1 an-232 1A0233 sp-1 an-233 1U0233 sp-1 an-233 1C0233 sp-1 an-233 1A0234 sp-1 an-234 1U0234 sp-1 an-234 1C0234 sp-1 an-234 1A0235 sp-1 an-235 1U0235 sp-1 an-235 1C0235 sp-1 an-235 1A0236 sp-1 an-236 1U0236 sp-1 an-236 1C0236 sp-1 an-236 1A0237 sp-1 an-237 1U0237 sp-1 an-237 1C0237 sp-1 an-237 1A0238 sp-1 an-238 1U0238 sp-1 an-238 1C0238 sp-1 an-238 1A0239 sp-1 an-239 1U0239 sp-1 an-239 1C0239 sp-1 an-239 1A0240 sp-1 an-240 1U0240 sp-1 an-240 1C0240 sp-1 an-240 1A0241 sp-1 an-241 1U0241 sp-1 an-241 1C0241 sp-1 an-241 1A0242 sp-1 an-242 1U0242 sp-1 an-242 1C0242 sp-1 an-242 1A0243 sp-1 an-243 1U0243 sp-1 an-243 1C0243 sp-1 an-243 1A0244 sp-1 an-244 1U0244 sp-1 an-244 1C0244 sp-1 an-244 1A0245 sp-1 an-245 1U0245 sp-1 an-245 1C0245 sp-1 an-245 1A0246 sp-1 an-246 1U0246 sp-1 an-246 1C0246 sp-1 an-246 1A0247 sp-1 an-247 1U0247 sp-1 an-247 1C0247 sp-1 an-247 1A0248 sp-1 an-248 1U0248 sp-1 an-248 1C0248 sp-1 an-248 1A0249 sp-1 an-249 1U0249 sp-1 an-249 1C0249 sp-1 an-249 1A0250 sp-1 an-250 1U0250 sp-1 an-250 1C0250 sp-1 an-250 1A0251 sp-1 an-251 1U0251 sp-1 an-251 1C0251 sp-1 an-251 1A0252 sp-1 an-252 1U0252 sp-1 an-252 1C0252 sp-1 an-252 1A0253 sp-1 an-253 1U0253 sp-1 an-253 1C0253 sp-1 an-253 1A0254 sp-1 an-254 1U0254 sp-1 an-254 1C0254 sp-1 an-254 1A0255 sp-1 an-255 1U0255 sp-1 an-255 1C0255 sp-1 an-255 1A0256 sp-1 an-258 1U0256 sp-1 an-256 1C0256 sp-1 an-256 1A0257 sp-1 an-257 1U0257 sp-1 an-257 1C0257 sp-1 an-257 1A0258 sp-1 an-258 1U0258 sp-1 an-258 1C0258 sp-1 an-258 1A0259 sp-1 an-259 1U0259 sp-1 an-259 1C0259 sp-1 an-259 1A0260 sp-1 an-260 1U0260 sp-1 an-260 1C0260 sp-1 an-260 1A0261 sp-1 an-261 1U0261 sp-1 an-261 1C0261 sp-1 an-261 1A0262 sp-1 an-262 1U0262 sp-1 an-262 1C0262 sp-1 an-262 1A0263 sp-1 an-263 1U0263 sp-1 an-263 1C0263 sp-1 an-263 1A0264 sp-1 an-264 1U0264 sp-1 an-264 1C0264 sp-1 an-264 1A0265 sp-1 an-265 1U0265 sp-1 an-265 1C0265 sp-1 an-265 1A0266 sp-1 an-266 1U0266 sp-1 an-266 1C0266 sp-1 an-266 1A0267 sp-1 an-267 1U0267 sp-1 an-267 1C0267 sp-1 an-267 1A0268 sp-1 an-268 1U0268 sp-1 an-268 1C0268 sp-1 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1A4021 sp-14 an-251 1U4021 sp-13 an-251 1A4022 sp-14 an-252 1U4022 sp-13 an-252 1A4023 sp-14 an-253 1U4023 sp-13 an-253 1A4024 sp-14 an-254 1U4024 sp-13 an-254 1A4025 sp-14 an-255 1U4025 sp-13 an-255 1A4026 sp-14 an-256 1U4026 sp-13 an-256 1A4027 sp-14 an-257 1U4027 sp-13 an-257 1A4028 sp-14 an-258 1U4028 sp-13 an-258 1A4029 sp-14 an-259 1U4029 sp-13 an-259 1A4030 sp-14 an-260 1U4030 sp-13 an-260 1A4031 sp-14 an-261 1U4031 sp-13 an-261 1A4032 sp-14 an-262 1U4032 sp-13 an-262 1A4033 sp-14 an-263 1U4033 sp-13 an-263 1A4034 sp-14 an-264 1U4034 sp-13 an-264 1A4035 sp-14 an-265 1U4035 sp-13 an-265 1A4036 sp-14 an-266 1U4036 sp-13 an-266 1A4037 sp-14 an-267 1U4037 sp-13 an-267 1A4038 sp-14 an-268 1U4038 sp-13 an-268 1A4039 sp-14 an-269 1U4039 sp-13 an-269 1A4040 sp-14 an-270 1U4040 sp-13 an-270 1A4041 sp-14 an-271 1U4041 sp-13 an-271 1A4042 sp-14 an-272 1U4042 sp-13 an-272 1A4043 sp-14 an-273 1U4043 sp-13 an-273 1A4044 sp-14 an-274 1U4044 sp-13 an-274 1A4045 sp-14 an-275 1U4045 sp-13 an-275 1A4045 sp-14 an-276 1U4046 sp-13 an-276 1A4047 sp-14 an-277 1U4047 sp-13 an-277 1A4048 sp-14 an-278 1U4048 sp-13 an-278 1A4049 sp-14 an-279 1U4049 sp-13 an-279 1A4050 sp-14 an-280 1U4050 sp-13 an-280 1A4051 sp-14 an-281 1U4051 sp-13 an-281 1A4052 sp-14 an-282 1U4052 sp-13 an-282 1A4053 sp-14 an-283 1U4053 sp-13 an-283 1A4054 sp-14 an-284 1U4054 sp-13 an-284 1A4055 sp-14 an-285 1U4055 sp-13 an-285 1A4056 sp-14 an-286 1U4056 sp-13 an-286 1A4057 sp-14 an-287 1U4057 sp-13 an-287 1A4058 sp-14 an-288 1U4058 sp-13 an-288 1A4059 sp-14 an-289 1U4059 sp-13 an-289 1A4060 sp-14 an-290 1U4060 sp-13 an-290 1A4061 sp-14 an-291 1U4061 sp-13 an-291 1A4062 sp-14 an-292 1U4062 sp-13 an-292 1A4063 sp-14 an-293 1U4063 sp-13 an-293 1A4064 sp-14 an-294 1U4064 sp-13 an-294 1A4065 sp-14 an-295 1U4065 sp-13 an-295 1A4066 sp-14 an-296 1U4066 sp-13 an-296 1A4067 sp-14 an-297 1U4067 sp-13 an-297 1A4068 sp-14 an-298 1U4068 sp-13 an-298 1A4069 sp-14 an-299 1U4069 sp-13 an-299 1A4070 sp-14 an-300 1U4070 sp-13 an-300 1A4071 sp-14 an-301 1U4071 sp-13 an-301 1A4072 sp-14 an-302 1U4072 sp-13 an-302 1A4073 sp-14 an-303 1U4073 sp-13 an-303 1A4074 sp-14 an-304 1U4074 sp-13 an-304 1A4075 sp-14 an-305 1U4075 sp-13 an-305 1A4076 sp-14 an-306 1U4076 sp-13 an-306 1A4077 sp-14 an-307 1U4077 sp-13 an-307 1A4078 sp-14 an-308 1U4078 sp-13 an-308 1A4079 sp-14 an-309 1U4079 sp-13 an-309 1A4080 sp-14 an-310 1U4080 sp-13 an-310 1A4081 sp-14 an-311 1U4081 sp-13 an-311 1A4082 sp-14 an-312 1U4082 sp-13 an-312 1A4083 sp-14 an-313 1U4083 sp-13 an-313 1A4084 sp-14 an-314 1U4084 sp-13 an-314 1A4085 sp-14 an-315 1U4085 sp-13 an-315 1A4086 sp-14 an-316 1U4086 sp-13 an-316 1A4087 sp-14 an-317 1U4087 sp-13 an-317 1A4088 sp-14 an-318 1U4088 sp-13 an-318 1A4089 sp-14 an-319 1U4089 sp-13 an-319 1A4090 sp-14 an-320 1U4090 sp-13 an-320 1A4091 sp-14 an-321 1U4091 sp-13 an-321 1A4092 sp-14 an-322 1U4092 sp-13 an-322 1A4093 sp-14 an-323 1U4093 sp-13 an-323 1A4094 sp-14 an-324 1U4094 sp-13 an-324 1A4095 sp-14 an-325 1U4095 sp-13 an-325 1A4096 sp-14 an-326 1U4096 sp-13 an-326 1A4097 sp-14 an-327 1U4097 sp-13 an-327 1A4098 sp-14 an-328 1U4098 sp-13 an-328 1A4099 sp-14 an-329 1U4099 sp-13 an-329 1A4100 sp-14 an-330 1U4100 sp-13 an-330 1A4101 sp-14 an-331 1U4101 sp-13 an-331 1A4102 sp-14 an-332 1U4102 sp-13 an-332 1A4103 sp-14 an-333 1U4103 sp-13 an-333 1A4104 sp-14 an-334 1U4104 sp-13 an-334 1A4105 sp-14 an-335 1U4105 sp-13 an-335 1A4106 sp-14 an-336 1U4106 sp-13 an-336 1A4107 sp-14 an-337 1U4107 sp-13 an-337 1A4108 sp-14 an-338 1U4108 sp-13 an-338 1A4109 sp-14 an-339 1U4109 sp-13 an-339 1A4110 sp-14 an-340 1U4110 sp-13 an-340 1A4111 sp-14 an-341 1U4111 sp-13 an-341 1A4112 sp-14 an-342 1U4112 sp-13 an-342 1A4113 sp-14 an-343 1U4113 sp-13 an-343 1A4114 sp-14 an-344 1U4114 sp-13 an-344 1A4115 sp-14 an-345 1U4115 sp-13 an-345 1A4116 sp-14 an-346 1U4116 sp-13 an-346 1A4117 sp-14 an-347 1U4117 sp-13 an-347 1A4118 sp-14 an-348 1U4118 sp-13 an-348 1A4119 sp-14 an-349 1U4119 sp-13 an-349 1A4120 sp-14 an-350 1U4120 sp-13 an-350 1A4121 sp-14 an-351 1U4121 sp-13 an-351 1A4122 sp-14 an-352 1U4122 sp-13 an-352 1A4123 sp-14 an-353 1U4123 sp-13 an-353 1A4124 sp-14 an-354 1U4124 sp-13 an-354 1A4125 sp-14 an-355 1U4125 sp-13 an-355 1A4126 sp-14 an-356 1U4126 sp-13 an-356 1A4127 sp-14 an-357 1U4127 sp-13 an-357 1A4128 sp-14 an-358 1U4128 sp-13 an-358 1A4129 sp-14 an-359 1U4129 sp-13 an-359 1A4130 sp-14 an-360 1U4130 sp-13 an-360 1A4131 sp-14 an-361 1U4131 sp-13 an-361 1A4132 sp-14 an-362 1U4132 sp-13 an-362 1A4133 sp-14 an-363 1U4133 sp-13 an-363 1A4134 sp-14 an-364 1U4134 sp-13 an-364 1A4135 sp-14 an-365 1U4135 sp-13 an-365 1A4136 sp-14 an-366 1U4136 sp-13 an-366 1A4137 sp-14 an-367 1U4137 sp-13 an-367 1A4138 sp-14 an-368 1U4138 sp-13 an-368 1A4139 sp-14 an-369 1U4139 sp-13 an-369 1A4140 sp-14 an-370 1U4140 sp-13 an-370 1A4141 sp-14 an-371 1U4141 sp-13 an-371 1A4142 sp-14 an-372 1U4142 sp-13 an-372 1A4143 sp-14 an-373 1U4143 sp-13 an-373 1A4144 sp-14 an-374 1U4144 sp-13 an-374 1A4145 sp-14 an-375 1U4145 sp-13 an-375 1A4146 sp-14 an-376 1U4146 sp-13 an-376 Y = NHCS 1A4147 sp-14 an-377 1U4147 sp-13 an-377

No Z N⁺R⁵R⁶R⁷ 1A4148 sp-15 an-1 1U4148 sp-14 an-1 1A5279 sp-19 an-1 1A4149 sp-15 an-2 1U4149 sp-14 an-2 1A5280 sp-19 an-2 1A4150 sp-15 an-3 1U4150 sp-14 an-3 1A5281 sp-19 an-3 1A4151 sp-15 an-4 1U4151 sp-14 an-4 1A5282 sp-19 an-4 1A4152 sp-15 an-5 1U4152 sp-14 an-5 1A5283 sp-19 an-5 1A4153 sp-15 an-6 1U4153 sp-14 an-6 1A5284 sp-19 an-6 1A4154 sp-15 an-7 1U4154 sp-14 an-7 1A5285 sp-19 an-7 1A4155 sp-15 an-8 1U4155 sp-14 an-8 1A5286 sp-19 an-8 1A4156 sp-15 an-9 1U4156 sp-14 an-9 1A5287 sp-19 an-9 1A4157 sp-15 an-10 1U4157 sp-14 an-10 1A5288 sp-19 an-10 1A4158 sp-15 an-11 1U4158 sp-14 an-11 1A5289 sp-19 an-11 1A4159 sp-15 an-12 1U4159 sp-14 an-12 1A5290 sp-19 an-12 1A4160 sp-15 an-13 1U4160 sp-14 an-13 1A5291 sp-19 an-13 1A4161 sp-15 an-14 1U4161 sp-14 an-14 1A5292 sp-19 an-14 1A4162 sp-15 an-15 1U4162 sp-14 an-15 1A5293 sp-19 an-15 1A4163 sp-15 an-16 1U4163 sp-14 an-16 1A5294 sp-19 an-16 1A4164 sp-15 an-17 1U4164 sp-14 an-17 1A5295 sp-19 an-17 1A4165 sp-15 an-18 1U4165 sp-14 an-18 1A5296 sp-19 an-18 1A4166 sp-15 an-19 1U4166 sp-14 an-19 1A5297 sp-19 an-19 1A4167 sp-15 an-20 1U4167 sp-14 an-20 1A5298 sp-19 an-20 1A4168 sp-15 an-21 1U4168 sp-14 an-21 1A5299 sp-19 an-21 1A4169 sp-15 an-22 1U4169 sp-14 an-22 1A5300 sp-19 an-22 1A4170 sp-15 an-23 1U4170 sp-14 an-23 1A5301 sp-19 an-23 1A4171 sp-15 an-24 1U4171 sp-14 an-24 1A5302 sp-19 an-24 1A4172 sp-15 an-25 1U4172 sp-14 an-25 1A5303 sp-19 an-25 1A4173 sp-15 an-26 1U4173 sp-14 an-26 1A5304 sp-19 an-26 1A4174 sp-15 an-27 1U4174 sp-14 an-27 1A5305 sp-19 an-27 1A4175 sp-15 an-28 1U4175 sp-14 an-28 1A5306 sp-19 an-28 1A4176 sp-15 an-29 1U4176 sp-14 an-29 1A5307 sp-19 an-29 1A4177 sp-15 an-30 1U4177 sp-14 an-30 1A5308 sp-19 an-30 1A4178 sp-15 an-31 1U4178 sp-14 an-31 1A5309 sp-19 an-31 1A4179 sp-15 an-32 1U4179 sp-14 an-32 1A5310 sp-19 an-32 1A4180 sp-15 an-33 1U4180 sp-14 an-33 1A5311 sp-19 an-33 1A4181 sp-15 an-34 1U4181 sp-14 an-34 1A5312 sp-19 an-34 1A4182 sp-15 an-35 1U4182 sp-14 an-35 1A5313 sp-19 an-35 1A4183 sp-15 an-36 1U4183 sp-14 an-36 1A5314 sp-19 an-36 1A4184 sp-15 an-37 1U4184 sp-14 an-37 1A5315 sp-19 an-37 1A4185 sp-15 an-38 1U4185 sp-14 an-38 1A5316 sp-19 an-38 1A4186 sp-15 an-39 1U4186 sp-14 an-39 1A5317 sp-19 an-39 1A4187 sp-15 an-40 1U4187 sp-14 an-40 1A5318 sp-19 an-40 1A4188 sp-15 an-41 1U4188 sp-14 an-41 1A5319 sp-19 an-41 1A4189 sp-15 an-42 1U4189 sp-14 an-42 1A5320 sp-19 an-42 1A4190 sp-15 an-43 1U4190 sp-14 an-43 1A5321 sp-19 an-43 1A4191 sp-15 an-44 1U4191 sp-14 an-44 1A5322 sp-19 an-44 1A4192 sp-15 an-45 1U4192 sp-14 an-45 1A5323 sp-19 an-45 1A4193 sp-15 an-46 1U4193 sp-14 an-46 1A5324 sp-19 an-46 1A4194 sp-15 an-47 1U4194 sp-14 an-47 1A5325 sp-19 an-47 1A4195 sp-15 an-48 1U4195 sp-14 an-48 1A5326 sp-19 an-48 1A4196 sp-15 an-49 1U4196 sp-14 an-49 1A5327 sp-19 an-49 1A4197 sp-15 an-50 1U4197 sp-14 an-50 1A5328 sp-19 an-50 1A4198 sp-15 an-51 1U4198 sp-14 an-51 1A5329 sp-19 an-51 1A4199 sp-15 an-52 1U4199 sp-14 an-52 1A5330 sp-19 an-52 1A4200 sp-15 an-53 1U4200 sp-14 an-53 1A5331 sp-19 an-53 1A4201 sp-15 an-54 1U4201 sp-14 an-54 1A5332 sp-19 an-54 1A4202 sp-15 an-55 1U4202 sp-14 an-55 1A5333 sp-19 an-55 1A4203 sp-15 an-56 1U4203 sp-14 an-56 1A5334 sp-19 an-56 1A4204 sp-15 an-57 1U4204 sp-14 an-57 1A5335 sp-19 an-57 1A4205 sp-15 an-58 1U4205 sp-14 an-58 1A5336 sp-19 an-58 1A4206 sp-15 an-59 1U4206 sp-14 an-59 1A5337 sp-19 an-59 1A4207 sp-15 an-60 1U4207 sp-14 an-60 1A5338 sp-19 an-60 1A4208 sp-15 an-61 1U4208 sp-14 an-61 1A5339 sp-19 an-61 1A4209 sp-15 an-62 1U4209 sp-14 an-62 1A5340 sp-19 an-62 1A4210 sp-15 an-63 1U4210 sp-14 an-63 1A5341 sp-19 an-63 1A4211 sp-15 an-64 1U4211 sp-14 an-64 1A5342 sp-19 an-64 1A4212 sp-15 an-65 1U4212 sp-14 an-65 1A5343 sp-19 an-65 1A4213 sp-15 an-66 1U4213 sp-14 an-66 1A5344 sp-19 an-66 1A4214 sp-15 an-67 1U4214 sp-14 an-67 1A5345 sp-19 an-67 1A4215 sp-15 an-68 1U4215 sp-14 an-68 1A5346 sp-19 an-68 1A4216 sp-15 an-69 1U4216 sp-14 an-69 1A5347 sp-19 an-69 1A4217 sp-15 an-70 1U4217 sp-14 an-70 1A5348 sp-19 an-70 1A4218 sp-15 an-71 1U4218 sp-14 an-71 1A5349 sp-19 an-71 1A4219 sp-15 an-72 1U4219 sp-14 an-72 1A5350 sp-19 an-72 1A4220 sp-15 an-73 1U4220 sp-14 an-73 1A5351 sp-19 an-73 1A4221 sp-15 an-74 1U4221 sp-14 an-74 1A5352 sp-19 an-74 1A4222 sp-15 an-75 1U4222 sp-14 an-75 1A5353 sp-19 an-75 1A4223 sp-15 an-76 1U4223 sp-14 an-76 1A5354 sp-19 an-76 1A4224 sp-15 an-77 1U4224 sp-14 an-77 1A5355 sp-19 an-77 1A4225 sp-15 an-78 1U4225 sp-14 an-78 1A5356 sp-19 an-78 1A4226 sp-15 an-79 1U4226 sp-14 an-79 1A5357 sp-19 an-79 1A4227 sp-15 an-80 1U4227 sp-14 an-80 1A5358 sp-19 an-80 1A4228 sp-15 an-81 1U4228 sp-14 an-81 1A5359 sp-19 an-81 1A4229 sp-15 an-82 1U4229 sp-14 an-82 1A5360 sp-19 an-82 1A4230 sp-15 an-83 1U4230 sp-14 an-83 1A5361 sp-19 an-83 1A4231 sp-15 an-84 1U4231 sp-14 an-84 1A5362 sp-19 an-84 1A4232 sp-15 an-85 1U4232 sp-14 an-85 1A5363 sp-19 an-85 1A4233 sp-15 an-86 1U4233 sp-14 an-86 1A5364 sp-19 an-86 1A4234 sp-15 an-87 1U4234 sp-14 an-87 1A5365 sp-19 an-87 1A4235 sp-15 an-88 1U4235 sp-14 an-88 1A5366 sp-19 an-88 1A4236 sp-15 an-89 1U4236 sp-14 an-89 1A5367 sp-19 an-89 1A4237 sp-15 an-90 1U4237 sp-14 an-90 1A5368 sp-19 an-90 1A4238 sp-15 an-91 1U4238 sp-14 an-91 1A5369 sp-19 an-91 1A4239 sp-15 an-92 1U4239 sp-14 an-92 1A5370 sp-19 an-92 1A4240 sp-15 an-93 1U4240 sp-14 an-93 1A5371 sp-19 an-93 1A4241 sp-15 an-94 1U4241 sp-14 an-94 1A5372 sp-19 an-94 1A4242 sp-15 an-95 1U4242 sp-14 an-95 1A5373 sp-19 an-95 1A4243 sp-15 an-96 1U4243 sp-14 an-96 1A5374 sp-19 an-96 1A4244 sp-15 an-97 1U4244 sp-14 an-97 1A5375 sp-19 an-97 1A4245 sp-15 an-98 1U4245 sp-14 an-98 1A5376 sp-19 an-98 1A4246 sp-15 an-99 1U4246 sp-14 an-99 1A5377 sp-19 an-99 1A4247 sp-15 an-100 1U4247 sp-14 an-100 1A5378 sp-19 an-100 1A4248 sp-15 an-101 1U4248 sp-14 an-101 1A5379 sp-19 an-101 1A4249 sp-15 an-102 1U4249 sp-14 an-102 1A5380 sp-19 an-102 1A4250 sp-15 an-103 1U4250 sp-14 an-103 1A5381 sp-19 an-103 1A4251 sp-15 an-104 1U4251 sp-14 an-104 1A5382 sp-19 an-104 1A4252 sp-15 an-105 1U4252 sp-14 an-105 1A5383 sp-19 an-105 1A4253 sp-15 an-106 1U4253 sp-14 an-106 1A5384 sp-19 an-106 1A4254 sp-15 an-107 1U4254 sp-14 an-107 1A5385 sp-19 an-107 1A4255 sp-15 an-108 1U4255 sp-14 an-108 1A5386 sp-19 an-108 1A4256 sp-15 an-109 1U4256 sp-14 an-109 1A5387 sp-19 an-109 1A4257 sp-15 an-110 1U4257 sp-14 an-110 1A5388 sp-19 an-110 1A4258 sp-15 an-111 1U4258 sp-14 an-111 1A5389 sp-19 an-111 1A4259 sp-15 an-112 1U4259 sp-14 an-112 1A5390 sp-19 an-112 1A4260 sp-15 an-113 1U4260 sp-14 an-113 1A5391 sp-19 an-113 1A4261 sp-15 an-114 1U4261 sp-14 an-114 1A5392 sp-19 an-114 1A4262 sp-15 an-115 1U4262 sp-14 an-115 1A5393 sp-19 an-115 1A4263 sp-15 an-116 1U4263 sp-14 an-116 1A5394 sp-19 an-116 1A4264 sp-15 an-117 1U4264 sp-14 an-117 1A5395 sp-19 an-117 1A4265 sp-15 an-118 1U4265 sp-14 an-118 1A5396 sp-19 an-118 1A4266 sp-15 an-119 1U4266 sp-14 an-119 1A5397 sp-19 an-119 1A4267 sp-15 an-120 1U4267 sp-14 an-120 1A5398 sp-19 an-120 1A4268 sp-15 an-121 1U4268 sp-14 an-121 1A5399 sp-19 an-121 1A4269 sp-15 an-122 1U4269 sp-14 an-122 1A5400 sp-19 an-122 1A4270 sp-15 an-123 1U4270 sp-14 an-123 1A5401 sp-19 an-123 1A4271 sp-15 an-124 1U4271 sp-14 an-124 1A5402 sp-19 an-124 1A4272 sp-15 an-125 1U4272 sp-14 an-125 1A5403 sp-19 an-125 1A4273 sp-15 an-126 1U4273 sp-14 an-126 1A5404 sp-19 an-126 1A4274 sp-15 an-127 1U4274 sp-14 an-127 1A5405 sp-19 an-127 1A4275 sp-15 an-128 1U4275 sp-14 an-128 1A5406 sp-19 an-128 1A4276 sp-15 an-129 1U4276 sp-14 an-129 1A5407 sp-19 an-129 1A4277 sp-15 an-130 1U4277 sp-14 an-130 1A5408 sp-19 an-130 1A4278 sp-15 an-131 1U4278 sp-14 an-131 1A5409 sp-19 an-131 1A4279 sp-15 an-132 1U4279 sp-14 an-132 1A5410 sp-19 an-132 1A4280 sp-15 an-133 1U4280 sp-14 an-133 1A5411 sp-19 an-133 1A4281 sp-15 an-134 1U4281 sp-14 an-134 1A5412 sp-19 an-134 1A4282 sp-15 an-135 1U4282 sp-14 an-135 1A5413 sp-19 an-135 1A4283 sp-15 an-136 1U4283 sp-14 an-136 1A5414 sp-19 an-136 1A4284 sp-15 an-137 1U4284 sp-14 an-137 1A5415 sp-19 an-137 1A4285 sp-15 an-138 1U4285 sp-14 an-138 1A5416 sp-19 an-138 1A4286 sp-15 an-139 1U4286 sp-14 an-139 1A5417 sp-19 an-139 1A4287 sp-15 an-140 1U4287 sp-14 an-140 1A5418 sp-19 an-140 1A4288 sp-15 an-141 1U4288 sp-14 an-141 1A5419 sp-19 an-141 1A4289 sp-15 an-142 1U4289 sp-14 an-142 1A5420 sp-19 an-142 1A4290 sp-15 an-143 1U4290 sp-14 an-143 1A5421 sp-19 an-143 1A4291 sp-15 an-144 1U4291 sp-14 an-144 1A5422 sp-19 an-144 1A4292 sp-15 an-145 1U4292 sp-14 an-145 1A5423 sp-19 an-145 1A4293 sp-15 an-146 1U4293 sp-14 an-146 1A5424 sp-19 an-146 1A4294 sp-15 an-147 1U4294 sp-14 an-147 1A5425 sp-19 an-147 1A4295 sp-15 an-148 1U4295 sp-14 an-148 1A5426 sp-19 an-148 1A4296 sp-15 an-149 1U4296 sp-14 an-149 1A5427 sp-19 an-149 1A4297 sp-15 an-150 1U4297 sp-14 an-150 1A5428 sp-19 an-150 1A4298 sp-15 an-151 1U4298 sp-14 an-151 1A5429 sp-19 an-151 1A4299 sp-15 an-152 1U4299 sp-14 an-152 1A5430 sp-19 an-152 1A4300 sp-15 an-153 1U4300 sp-14 an-153 1A5431 sp-19 an-153 1A4301 sp-15 an-154 1U4301 sp-14 an-154 1A5432 sp-19 an-154 1A4302 sp-15 an-155 1U4302 sp-14 an-155 1A5433 sp-19 an-155 1A4303 sp-15 an-156 1U4303 sp-14 an-156 1A5434 sp-19 an-156 1A4304 sp-15 an-157 1U4304 sp-14 an-157 1A5435 sp-19 an-157 1A4305 sp-15 an-158 1U4305 sp-14 an-158 1A5436 sp-19 an-158 1A4306 sp-15 an-159 1U4306 sp-14 an-159 1A5437 sp-19 an-159 1A4307 sp-15 an-160 1U4307 sp-14 an-160 1A5438 sp-19 an-160 1A4308 sp-15 an-161 1U4308 sp-14 an-161 1A5439 sp-19 an-161 1A4309 sp-15 an-162 1U4309 sp-14 an-162 1A5440 sp-19 an-162 1A4310 sp-15 an-163 1U4310 sp-14 an-163 1A5441 sp-19 an-163 1A4311 sp-15 an-164 1U4311 sp-14 an-164 1A5442 sp-19 an-164 1A4312 sp-15 an-165 1U4312 sp-14 an-165 1A5443 sp-19 an-165 1A4313 sp-15 an-166 1U4313 sp-14 an-166 1A5444 sp-19 an-166 1A4314 sp-15 an-167 1U4314 sp-14 an-167 1A5445 sp-19 an-167 1A4315 sp-15 an-168 1U4315 sp-14 an-168 1A5446 sp-19 an-168 1A4316 sp-15 an-169 1U4316 sp-14 an-169 1A5447 sp-19 an-169 1A4317 sp-15 an-170 1U4317 sp-14 an-170 1A5448 sp-19 an-170 1A4318 sp-15 an-171 1U4318 sp-14 an-171 1A5449 sp-19 an-171 1A4319 sp-15 an-172 1U4319 sp-14 an-172 1A5450 sp-19 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1U5197 sp-20 an-296 1A6328 sp-22 an-296 1A5198 sp-18 an-297 1U5198 sp-20 an-297 1A6329 sp-22 an-297 1A5199 sp-18 an-298 1U5199 sp-20 an-298 1A6330 sp-22 an-298 1A5200 sp-18 an-299 1U5200 sp-20 an-299 1A6331 sp-22 an-299 1A5201 sp-18 an-300 1U5201 sp-20 an-300 1A6332 sp-22 an-300 1A5202 sp-18 an-301 1U5202 sp-20 an-301 1A6333 sp-22 an-301 1A5203 sp-18 an-302 1U5203 sp-20 an-302 1A6334 sp-22 an-302 1A5204 sp-18 an-303 1U5204 sp-20 an-303 1A6335 sp-22 an-303 1A5205 sp-18 an-304 1U5205 sp-20 an-304 1A6336 sp-22 an-304 1A5206 sp-18 an-305 1U5206 sp-20 an-305 1A6337 sp-22 an-305 1A5207 sp-18 an-306 1U5207 sp-20 an-306 1A6338 sp-22 an-306 1A5208 sp-18 an-307 1U5208 sp-20 an-307 1A6339 sp-22 an-307 1A5209 sp-18 an-308 1U5209 sp-20 an-308 1A6340 sp-22 an-308 1A5210 sp-18 an-309 1U5210 sp-20 an-309 1A6341 sp-22 an-309 1A5211 sp-18 an-310 1U5211 sp-20 an-310 1A6342 sp-22 an-310 1A5212 sp-18 an-311 1U5212 sp-20 an-311 1A6343 sp-22 an-311 1A5213 sp-18 an-312 1U5213 sp-20 an-312 1A6344 sp-22 an-312 1A5214 sp-18 an-313 1U5214 sp-20 an-313 1A6345 sp-22 an-313 1A5215 sp-18 an-314 1U5215 sp-20 an-314 1A6346 sp-22 an-314 1A5216 sp-18 an-315 1U5216 sp-20 an-315 1A6347 sp-22 an-315 1A5217 sp-18 an-316 1U5217 sp-20 an-316 1A6348 sp-22 an-316 1A5218 sp-18 an-317 1U5218 sp-20 an-317 1A6349 sp-22 an-317 1A5219 sp-18 an-318 1U5219 sp-20 an-318 1A6350 sp-22 an-318 1A5220 sp-18 an-319 1U5220 sp-20 an-319 1A6351 sp-22 an-319 1A5221 sp-18 an-320 1U5221 sp-20 an-320 1A6352 sp-22 an-320 1A5222 sp-18 an-321 1U5222 sp-20 an-321 1A6353 sp-22 an-321 1A5223 sp-18 an-322 1U5223 sp-20 an-322 1A6354 sp-22 an-322 1A5224 sp-18 an-323 1U5224 sp-20 an-323 1A6355 sp-22 an-323 1A5225 sp-18 an-324 1U5225 sp-20 an-324 1A6356 sp-22 an-324 1A5226 sp-18 an-325 1U5226 sp-20 an-325 1A6357 sp-22 an-325 1A5227 sp-18 an-326 1U5227 sp-20 an-326 1A6358 sp-22 an-326 1A5228 sp-18 an-327 1U5228 sp-20 an-327 1A6359 sp-22 an-327 1A5229 sp-18 an-328 1U5229 sp-20 an-328 1A6360 sp-22 an-328 1A5230 sp-18 an-329 1U5230 sp-20 an-329 1A6361 sp-22 an-329 1A5231 sp-18 an-330 1U5231 sp-20 an-330 1A6362 sp-22 an-330 1A5232 sp-18 an-331 1U5232 sp-20 an-331 1A6363 sp-22 an-331 1A5233 sp-18 an-332 1U5233 sp-20 an-332 1A6364 sp-22 an-332 1A5234 sp-18 an-333 1U5234 sp-20 an-333 1A6365 sp-22 an-333 1A5235 sp-18 an-334 1U5235 sp-20 an-334 1A6366 sp-22 an-334 1A5236 sp-18 an-335 1U5236 sp-20 an-335 1A6367 sp-22 an-335 1A5237 sp-18 an-336 1U5237 sp-20 an-336 1A6368 sp-22 an-336 1A5238 sp-18 an-337 1U5238 sp-20 an-337 1A6369 sp-22 an-337 1A5239 sp-18 an-338 1U5239 sp-20 an-338 1A6370 sp-22 an-338 1A5240 sp-18 an-339 1U5240 sp-20 an-339 1A6371 sp-22 an-339 1A5241 sp-18 an-340 1U5241 sp-20 an-340 1A6372 sp-22 an-340 1A5242 sp-18 an-341 1U5242 sp-20 an-341 1A6373 sp-22 an-341 1A5243 sp-18 an-342 1U5243 sp-20 an-342 1A6374 sp-22 an-342 1A5244 sp-18 an-343 1U5244 sp-20 an-343 1A6375 sp-22 an-343 1A5245 sp-18 an-344 1U5245 sp-20 an-344 1A6376 sp-22 an-344 1A5246 sp-18 an-345 1U5246 sp-20 an-345 1A6377 sp-22 an-345 1A5247 sp-18 an-346 1U5247 sp-20 an-346 1A6378 sp-22 an-346 1A5248 sp-18 an-347 1U5248 sp-20 an-347 1A6379 sp-22 an-347 1A5249 sp-18 an-348 1U5249 sp-20 an-348 1A6380 sp-22 an-348 1A5250 sp-18 an-349 1U5250 sp-20 an-349 1A6381 sp-22 an-349 1A5251 sp-18 an-350 1U5251 sp-20 an-350 1A6382 sp-22 an-350 1A5252 sp-18 an-351 1U5252 sp-20 an-351 1A6383 sp-22 an-351 1A5253 sp-18 an-352 1U5253 sp-20 an-352 1A6384 sp-22 an-352 1A5254 sp-18 an-353 1U5254 sp-20 an-353 1A6385 sp-22 an-353 1A5255 sp-18 an-354 1U5255 sp-20 an-354 1A6386 sp-22 an-354 1A5256 sp-18 an-355 1U5256 sp-20 an-355 1A6387 sp-22 an-355 1A5257 sp-18 an-356 1U5257 sp-20 an-356 1A6388 sp-22 an-356 1A5258 sp-18 an-357 1U5258 sp-20 an-357 1A6389 sp-22 an-357 1A5259 sp-18 an-358 1U5259 sp-20 an-358 1A6390 sp-22 an-358 1A5260 sp-18 an-359 1U5260 sp-20 an-359 1A6391 sp-22 an-359 1A5261 sp-18 an-360 1U5261 sp-20 an-360 1A6392 sp-22 an-360 1A5262 sp-18 an-361 1U5262 sp-20 an-361 1A6393 sp-22 an-361 1A5263 sp-18 an-362 1U5263 sp-20 an-362 1A6394 sp-22 an-362 1A5264 sp-18 an-363 1U5264 sp-20 an-363 1A6395 sp-22 an-363 1A5265 sp-18 an-364 1U5265 sp-20 an-364 1A6396 sp-22 an-364 1A5266 sp-18 an-365 1U5266 sp-20 an-365 1A6397 sp-22 an-365 1A5267 sp-18 an-366 1U5267 sp-20 an-366 1A6398 sp-22 an-366 1A5268 sp-18 an-367 1U5268 sp-20 an-367 1A6399 sp-22 an-367 1A5269 sp-18 an-368 1U5269 sp-20 an-368 1A6400 sp-22 an-368 1A5270 sp-18 an-369 1U5270 sp-20 an-369 1A6401 sp-22 an-369 1A5271 sp-18 an-370 1U5271 sp-20 an-370 1A6402 sp-22 an-370 1A5272 sp-18 an-371 1U5272 sp-20 an-371 1A6403 sp-22 an-371 1A5273 sp-18 an-372 1U5273 sp-20 an-372 1A6404 sp-22 an-372 1A5274 sp-18 an-373 1U5274 sp-20 an-373 1A6405 sp-22 an-373 1A5275 sp-18 an-374 1U5275 sp-20 an-374 1A6406 sp-22 an-374 1A5276 sp-18 an-375 1U5276 sp-20 an-375 1A6407 sp-22 an-375 1A5277 sp-18 an-376 1U5277 sp-20 an-376 1A6408 sp-22 an-376 1A5278 sp-18 an-377 1U5278 sp-20 an-377 1A6409 sp-22 an-377 End of Table 1

Further, mention may be made of compounds (from 2A0001 to 2A6409, from 2U0001 to 2U5278, and from 2C0001 to 2C3770) that are identical to the compounds described in Table 1 (from 1A0001 to 1A6409, from 1U001 to 1U5278, and from 1CO₀₀₁ to 1C3770) except that the bonding position of Y has been changed to the para-position. Here, it means that, for example, compound 1A0001 has been changed to compound 2A0001. The same is true for the following.

Further, mention may be made of compounds (from 3A0001 to 3A6409, from 3U0001 to 3U5278, and from 3C0001 to 3C3770) that are identical to the compounds described in Table 1 (f from 1A001 to 1A6409, from 1U0001 to 1U5278, and from 1C0001 to 1C3770) except that the NR³R⁴ has been changed to a 7-diethylamino group.

Further, mention may be made of compounds (from 4A0001 to 4A6409, from 4U0001 to 4U5278, and from 4C0001 to 4C3770) that are identical to the compounds described in Table 1 (from 1A0001 to 1A6409, from 1U0001 to 1U5278, and from 1C0001 to 1 C3770) except that the NR³R⁴ has been changed to a 7-ethylmethylamino group.

Further, mention may be made of compounds (from 5A0001 to 5A6409, from 5U0001 to 5U5278, and from 5C0001 to 5C3770) that correspond to the compounds described in Table 1 (from 1A0001 to 1A6409, from 1U0001 to 1U5278, and from 1C0001 to 1C3770) except that the NR³R⁴ has been changed to a 9-dimethylamino group.

Further, mention may be made of compounds (from 6A0001 to 6A6409, from 6U0001 to 6U5278, and from 6C0001 to 6C3770) that are identical to the compounds described in Table 1 (from 1A001 to 1A6409, from 1U0001 to 1U5278, and from 1C0001 to 1C3770) except that the NR³R⁴ has been changed to a 7,9-bis(dimethylamino) group.

Further, mention may be made of compounds (from 7A0001 to 7A6409, from 7U0001 to 7U5278, and from 7C0001 to 7C3770) that are identical to the compounds described in Table 1 (from 1A001 to 1A6409, from 1U0001 to 1 U5278, and from 1C001 to 1C3770) except that both R¹ and R² have been changed to a propyl group.

Further, mention may be made of compounds (from 8A0001 to 8A6409, from 8U0001 to 8U5278, and from 8C0001 to 8C3770) that are identical to the compounds described in Table 1 (from 1A0001 to 1A6409, from 1U0001 to 1U5278, and from 1C0001 to 1C3770) except that both R¹ and R² have been changed to a pentyl group.

Further, mention may be made of compounds (from 9A0001 to 9A6409, from 9U0001 to 9U5278, and from 9C0001 to 9C3770) that are identical to the compounds described in Table 1 (from 1A0001 to 1A6409, from 1 U0001 to 1 U5278, and from 1 C0001 to 1 C3770) except that both R¹ and R² have been changed to a hexyl group.

Further, mention may be made of compounds (from 10A0001 to 10A6409, from 10U0001 to 10U5278, and from 10C0001 to 10C3770) that are identical to the compounds described in (from 1A0001 to 1A6409, from 1U0001 to 1U5278, and from 1C0001 to 1C3770) except that the R¹ thereof has been changed to an ethyl group.

The compounds represented by the formula (1) of the present invention can be produced by the following production method.

(Production Method)

To obtain those compounds in which Y is an —NHCS— among the compounds represented by formula (1), a compound represented by the formula (3) below

[wherein R¹, R², R³, R⁴, m, n, and Z are as mentioned earlier, Y represents an —NHCS—, and X represents a group that can become an anion] is allowed to react with a compound represented by formula (2) below

[wherein R⁵, R⁶, and R⁷ are as mentioned earlier, and the quaternary ammonium structure mentioned earlier has been changed to a tertiary amine structure].

The reaction is carried out, for example, at room temperature or 40 to 100° C. optionally in a solvent such as acetonitrile or N,N-dimethylformamide (hereinafter, “DMF” for short) by allowing at least an equimolar amount, preferably 1 to 5 time molar amount of the compound represented by the formula (2) to react with the compound represented by the formula (3) for 1 to 48 hours.

X in the formula (3) is a group that undergoes nucleophilic substitution by the compound represented by the formula (2) and is released as an anion, preferably a group that is released as a pharmaceutically acceptable anion. Preferable examples thereof include F, Cl, Br, I, mesylate, and tosylate, and more preferably Cl, Br, and I.

Compounds represented by the formula (2) include compounds represented by formulae from (ta-1) to (ta-377). Letters next to the formula numbers indicate names of manufacturing companies as follows. “AC” stands for ACROSS ORGANICS, “AL” stands for ALDRICH CHEMICAL COMPANY, “BO” stands for BIO-NET CHEMICAL CO. LTD., “FL” stands for FLUKA CHEMICAL CORPORATION, “IC” stands for ICN-RF, “LN” stands for LANCASTER CHEMICAL CO. LTD., “MY” stands for MAYBRIDGE CHEMICALS, “NC” stands for NACALAI CO. LTD., “PF” stands for PFALZ & BAUER, “SG” stands for SIGMA CHEMICAL COMPANY, “SL” stands for SALOR CHEMICAL COMPANY, “TK” stands for TOKYO CHEMICAL INDUSTRIES, LTD., “WK” stands for WAKO PURE CHEMICAL INDUSTRIES LTD., and “WT” stands for WATANABE CHEMICAL INDUSTRIES LTD. ta-37 is prepared by allowing benzyl bromide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with dipropylamine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-56 is prepared by allowing 3-bromopropanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with dibutylamine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-57 is prepared by allowing 4-bromobutanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with dibutylamine in the presence of potassium carbonate. ta-117 is prepared by neutralizing its hydrochloride manufactured by SALOR CHEMICAL COMPANY. ta-137 is prepared by allowing benzyl bromide to react with N-ethyl ethanolamine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-138 is prepared by allowing benzyl bromide to react with N-propylethanolamine manufactured by ALDRICH CHEMICAL COMPANY in the presence of potassium carbonate. ta-139 is prepared by allowing benzyl bromide to react with N-butylethanolamine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-145 is prepared by neutralizing a hydrochloride manufactured by ALDRICH CHEMICAL COMPANY. ta-148 is prepared by neutralizing its hydrochloride manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. ta-152 is prepared by allowing benzyl bromide to react with ta-99. ta-153 is prepared by allowing benzyl bromide to react with ta-100. ta-154 is prepared by allowing benzyl bromide to react with ta-101. ta-155 is prepared by allowing benzyl bromide to react with ta-105. ta-156 is prepared by allowing benzyl bromide to react with ta-106. ta-157 is prepared by allowing benzyl bromide to react with ta-108. ta-158 is prepared by allowing benzyl bromide to react with ta-112. ta-162 is prepared by allowing pentyl iodide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with pyrrolidine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-172 is prepared by neutralizing its hydrochloride manufactured by MAYBRIDGE CHEMICALS. ta-178 is prepared by neutralizing its hydrochloride manufactured by NACALAI CO. LTD. ta-181 is prepared by allowing butyl iodide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with piperidine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-182 is prepared by allowing pentyl iodide to react with piperidine in the presence of potassium carbonate. ta-185 is prepared by allowing benzyl bromide to react with piperidine in the presence of potassium carbonate. ta-193 is prepared by allowing sodium borohydride to react with ta-207. ta-212 is prepared by neutralizing its hydrochloride manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. ta-234 is prepared by allowing pentyl iodide to react with morpholine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-237 is prepared by allowing benzyl bromide to react with morpholine in the presence of potassium carbonate. ta-255 is prepared by allowing ethyl iodide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with piperazine manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-256 is prepared by allowing butyl iodide to react with piperazine in the presence of potassium carbonate. ta-257 is manufactured by allowing pentyl iodide to react with piperazine in the presence of potassium carbonate. ta-259 is prepared by allowing benzyl bromide to react with piperazine in the presence of potassium carbonate. ta-264 is prepared by allowing benzyl bromide to react with ta-254. ta-265 is prepared by allowing benzyl bromide to react with ta-256. ta-266 is prepared by allowing benzyl bromide to react with ta-260. ta-279 is prepared by allowing butyl iodide to react with azepane manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-280 is prepared by allowing pentyl iodide to react with azepane in the presence of potassium carbonate. ta-281 is prepared by allowing benzyl bromide to react with azepane in the presence of potassium carbonate. ta-290 is prepared by neutralizing its hydrochloride manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. ta-294 is prepared by allowing phenylacetyl chloride manufactured by ALDRICH CHEMICAL COMPANY to react with 3-aminoquinuclidine hydrochloride manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in the presence of potassium carbonate. ta-295 is prepared by allowing butyl chloride manufactured by ALDRICH CHEMICAL COMPANY to react with 3-aminoquinuclidine hydrochloride in the presence of potassium carbonate. ta-296 is prepared by allowing valeryl chloride manufactured by ALDRICH CHEMICAL COMPANY to react with 3-aminoquinuclidine hydrochloride in the presence of potassium carbonate. ta-298 is prepared by allowing butyl bromide manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. to react with ta-297. ta-299 is prepared by allowing benzyl bromide to react with ta-297. (ta-1) to (ta-377) correspond to (an-1) to (an-377) mentioned earlier, respectively.

The compounds represented by formula (3) are obtained by allowing compounds represented in formula (4-1) below

[wherein R¹, R², R³, R⁴, m, n, Z, and X are as mentioned earlier; Y′ represents an —NHCO—, provided that —NH in the —NHCO— represents a bond that links with an adjacent benzene ring and CO— represents a bond that links with an adjacent Z] to react with various sulfurizing agents.

The reaction is carried out, for example, at room temperature or 50 to 100° C. in a solvent such as tetrahydrofuran (hereinafter, “THF” for short), 1,4-dioxane, or toluene, by allowing the compound represented by the formula (4-1) to react with at least an equimolar amount, preferably 1 to 10 time molar amount of a sulfurizing agent for 1 to 48 hours. Examples of preferable sulfurizing solvent include Lawesson's reagent (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) and diphosphorus pentasulfide (manufactured by WAKO PURE CHEMICAL INDUSTRIES).

The substituting position of Y′ in the formula (4-1) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position, and most preferably a meta-position. To obtain the compound represented by formula (4-1), a compound represented by the following formula (6-1)

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier] is allowed to react with a compound represented by the following formula (5-1)

[wherein n, Z, and X are as mentioned earlier and L¹ represents a leaving group].

The reaction is carried out, for example, by allowing at least an equimolar amount, preferably 1 to 1.2 time molar amount of the compound represented by the formula (5-1) to react with the compound represented by the formula (6-1), in a solvent such as dichloromethane or THF in the presence of an excess amount, preferably 1.5 to 3 time molar amount of a base, preferably an organic base such as triethylamine or an inorganic base such as potassium carbonate, at room temperature to 60° C. for 1 to 48 hours.

L¹ in the formula (5-1) is a group that undergoes nucleophilic substitution by the compound represented by the formula (6-1) and is released. Preferable examples of such a group include F, Cl, Br, I, mesylate and tosylate, with Cl and Br being more preferable. L¹ and X may be mutually different, but it is also preferable that L¹ and X are equal to each other. Examples of preferable compounds represented by the formula (5-1) include 3-bromopropionyl chloride (ac-1), 4-bromobutyryl chloride (ac-2), 5-bromovaleryl chloride (ac-3), 6-bromo-n-caproyl chloride (ac-4) (all of from ta-1 to ta-4 are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 7-bromo-n-heptanoyl chloride (ac-5), (prepared by oxidizing 7-bromo-1-heptanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. with chromium (VI) oxide in the presence of concentrated sulfuric acid and then allowing thionyl chloride to react with the resultant), 8-bromo-n-octanoyl chloride (ac-6) (prepared by allowing thionyl chloride to react with 8-bromooctanoic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 9-bromo-n-nonanoyl chloride (ac-7) (prepared by oxidizing 9-bromo-1-nonanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. with chromium oxide (VI) in the presence of concentrated sulfuric acid and then allowing thionyl chloride to react with the resultant), 10-bromo-n-decanoyl chloride (ac-8) (prepared by allowing thionyl chloride to react with 10-bromodecanoic acid manufactured by PFALZ & BAUER), 11-bromoundecanoyl chloride (ac-9) (prepared by allowing thionyl chloride to react with 11-bromoundecanoic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 3-bromo-2-methylpropionyl chloride (ac-10) (prepared by allowing thionyl chloride to react with 3-bromo-2-methylpropionic acid manufactured by FLUKA CHEMICAL CORPORATION), 4-(chloromethyl)benzoyl chloride (ac-11) (manufactured by ALDRICH CHEMICAL COMPANY), 4-(bromomethyl)phenylacetyl chloride (ac-12) (prepared by allowing thionyl chloride to react with 4-(bromomethyl) phenylacetic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 2-[4-(bromomethyl)phenyl]propionyl chloride (ac-13) (prepared by allowing thionyl chloride to react with 2-[4-(bromomethyl)phenyl]propionic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 3-(bromomethyl)phenoxyacetyl chloride (ac-14) (prepared by allowing thionyl chloride to react with 3-(bromomethyl)phenoxyacetic acid manufactured by LANCASTER), 3-bromo-2-(bromomethyl)propionyl chloride (ac-15) (prepared by allowing thionyl chloride to react with 3-bromo-2-(bromomethyl)propionic acid manufactured by ALDRICH CHEMICAL COMPANY), 3-bromoacryloyl chloride (ac-16) (prepared by allowing thionyl chloride to react with 3-bromoacrylic acid manufactured by MAYBRIDGE CHEMICALS), and 3-(bromomethyl)crotonyl chloride (ac-17) (prepared by allowing thionyl chloride to react with 3-(bromomethyl)crotonic acid manufactured by SALOR CHEMICAL COMPANY).

The substituting position of a primary amino group in the formula (6-1) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position and more preferably a meta-position.

To obtain those compounds in which Y represents —NHCS— among the compounds represented by formula (1), compounds represented by the following formula (4-2)

[wherein R¹, R², R³, R⁴, m, n, R⁵, R⁶, R⁷, Y′, Z, and X⁻ are as mentioned earlier] are allowed to react with various sulfurizing agents.

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 10 time molar amount of the sulfurizing agent to react with the compound represented by the formula (4-2) in a solvent such as ethanol, 1,4-dioxane, chloroform or 1,2-dichloroethane, at room temperature or at 50° C. to 100° C., for 1 to 48 hours. Examples of a preferable sulfurizing agent include Lawesson's reagent and diphosphorus pentasulfide.

The compound represented by the formula (4-2) is obtained by allowing the compound represented by the formula (2) to react with the compound represented by the formula (4-1).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 5 time molar amount of the compound represented by the formula (2) to react with the compound represented by the formula (4-1) optionally in a solvent such as acetonitrile or DMF, at room temperature or 40 to 100° C. for 1 to 48 hours.

To obtain those compounds in which Y represents —NHCSNH—among the compounds represented by formula (1), a compound represented by formula (6-1)

[wherein n, R⁵, R⁶, R⁷, Z, and X⁻ are as mentioned earlier] is allowed to react with a compound represented by formula (5-2a).

The reaction is carried out, for example, by allowing an equimolar amount of the compound represented by the formula (5-2a) to react with the compound represented by the formula (6-1) in a solvent such as chloroform, acetonitrile, or DMF at room temperature or at a temperature of from 40° C. to 100° C. for 1 to 48 hours.

The compound represented by the formula (5-2a) can be obtained by allowing the compound represented by the formula (2) to react with a compound represented by formula (5-2b) below

[wherein n, Z, and X are as mentioned earlier.]

The reaction is carried out, for example, by allowing at least equimolar amount, preferably 1 to 5 time molar amount of the compound represented by the formula (2) to react with the compound represented by the formula (5-2b) optionally in a solvent such as acetonitrile or DMF at room temperature or at 40° C. to 100° C. for 1 to 48 hours.

Examples of the compound represented by the formula (5-2b) include 2-bromoethyl isothiocyanate (is-1), 3-bromopropyl isothiocyanate (is-2), (both is-1 and is-2 are manufactured by TRANS WORLD CHEMICAL CORPORATION), 4-bromobutyl isothiocyanate (is-3) (prepared by brominating 4-aminobutanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. with hydrobromic acid and then allowing thiophosgene to react with the resultant according to the method described in Canadian Journal of Chemistry, Vol. 49, 971-974, 1971), 5-bromopentyl isothiocyanate (is-4) (prepared similarly from 5-aminopentanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 6-bromohexyl isothiocyanate (is-5) (prepared similarly from 6-aminohexanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 7-bromoheptyl isothiocyanate (is-6) (prepared similarly from 7-aminoheptanol manufactured by WATANABE CHEMICAL INDUSTRIES LTD.), 8-bromooctyl isothiocyanate (is-7) (prepared similarly from 8-aminooctanol manufactured by WATANABE CHEMICAL INDUSTRIES LTD.), 9-bromononyl isothiocyanate (is-8) (prepared similarly from 9-aminononanol manufactured by WATANABE CHEMICAL INDUSTRIES LTD.), 10-bromodecyl isothiocyanate (is-9) (prepared similarly from 10-aminodecanol manufactured by WATANABE CHEMICAL INDUSTRIES LTD.), 3-bromo-2,2-dimethylpropyl isothiocyanate (is-10) (prepared similarly from 3-amino-2,2-dimethylpropanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 5-bromo-4,4-dimethylpentyl isothiocyanate (is-11) (prepared similarly from 5-amino-2,2-dimethylpentanol manufactured by ICN-RF, 2-(2-bromoethoxy)ethyl isothiocyanate (is-12) (prepared similarly from 2-(2-aminoethoxy)ethanol manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 2,2-bis(bromomethyl)butyl isothiocyanate (is-13) (prepared similarly from 2-(aminoethyl)-2-ethyl-1,3-propanediol manufactured by SALOR CHEMICAL COMPANY), and 4-(bromomethyl)phenyl isothiocyanate (is-14) (prepared from p-tolyl isothiocyanate manufactured by ALDRICH CHEMICAL COMPANY according to the method described in Journal of Heterocyclic Chemistry, Vol. 31, 457-480, 1994).

To obtain those compounds in which Y represents —NHCSO— among the compounds represented by formula (1), a compound represented by the following formula (6-2)

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier.] is allowed to react with a compound represented by the following formula (5-3a).

[wherein n, R⁵, R⁶, R⁷, Z, and X— are as mentioned earlier.]

The reaction is carried out, for example, by allowing an equimolar amount of the compound represented by the formula (5-3a) to react with the compound represented by the formula (6-2) in a solvent such as THF, 1,4-dioxane, or 2-ethoxyethyl ether in the presence of an equimolar amount or more, preferably 1 to 5 time molar amount of a base, preferably an inorganic base such as sodium hydride or metallic sodium at 50° C. to 100° C., for 1 to 48 hours.

The substituting position of —NCS in the formula (6-2) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position, and most preferably a meta-position.

The compound represented by the formula (5-3a) are obtained by allowing the compound represented by the formula (2) to react with a compound represented by formula (5-3b).

[Chemical Formula 47] HO—Z—(X)n  (5-3 b) [wherein n, Z, and X are as mentioned earlier.]

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 5 time molar amount of the compound represented by the formula (2) to react with the compound represented by the formula (5-3b), optionally in a solvent such as acetonitrile or DMF, at room temperature or at 40° C. to 100° C. for 1 to 48 hours.

Examples of compounds represented by the formula (5-3b) include 2-bromoethanol (al-1), 3-bromopropanol (al-2), 4-bromobutanol (al-3), 5-bromopentanol (al-4), 6-bromohexanol (al-5), 7-bromoheptanol (al-6), 8-bromooctanol (al-7), 9-bromononanol (al-8), 10-bromodecanol (al-9) (all the compounds from al-1 to al-9 are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), 3-bromo-2-methylpropanol (al-10), 3-bromo-2,2-dimethylpropanol (al-11) (the compounds al-10 and al-11 are manufactured by ALDRICH CHEMICAL COMPANY).

The compound represented by the formula (6-2) is obtained by allowing thiophosgene to react with the compound represented by the formula (6-1).

The reaction is carried out, for example, by allowing an equimolar amount of thiophosgene (manufactured by ALDRICH CHEMICAL COMPANY) to react with the compound represented by the formula (6-1), optionally in a solvent such as THF or dichloromethane, in the presence of an equimolar amount or more, preferably 1 to 5 time molar amount of a base, preferably an organic base such as triethylamine, at room temperature or 0 to 10° C. for 1 to 24 hours.

The compound represented by the formula (6-1) is obtained by subjecting a compound represented by formula (7-2a) below

[wherein R¹, R², R³, R⁴ and m are as mentioned earlier] to hydrogenation, reaction with hydroxylamine, or acid hydrolysis according to the method described in literature (Tetrahedron Letters, Vol. 38, 6367-6370, 1997).

In the case of the hydrogenation, the reaction is carried out, for example, by addition of hydrogen gas to the compound represented by the formula (7-2a) in a solvent such as methanol, ethyl acetate, or 1,4-dioxane in the presence of 1 mole % to 30 mole % of a catalytic reduction catalyst, at room temperature or at 40° C. to 100° for 1 to 24 hours. Examples of a preferable catalytic reduction catalyst include palladium and platinum.

In the case of the reaction with hydroxylamine, the reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 3 time molar amount of hydroxylamine hydrochloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) to react with the compound represented by the formula (7-2a) in a solvent such as methanol in the presence of an equimolar or more, preferably 1 to 5 time molar amount of a base such as sodium acetate at room temperature for 1 to 24 hours.

In the case of acid hydrolysis, the reaction is carried out, for example, by allowing an excess amount, preferably 30 to 300 time molar amount of an acid, preferably 1 N to 5 N hydrochloric acid, to react with the compound represented by the formula (7-2a), optionally in a solvent such as THF or methanol, at room temperature for 1 to 24 hours.

The substituting position of the imino group in the formula (7-2a) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position.

The compound represented by the formula (7-2a) is obtained by allowing benzophenonimine to react with a compound represented by formula (7-2b) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier.]

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 5 time molar amount of benzophenonimine (manufactured by ALDRICH CHEMICAL COMPANY) to react with the compound represented by the formula (7-2b) in a solvent such as THF, 1,4-dioxane, or toluene, in the presence of an organic palladium compound such as 0.1 mole % to 10 mole % of palladium (II) acetate, an organic phosphorus compound such as 0.1 mole % to 10 mole % of 2,2′-bis(diphenylphosphenyl)-1,1′-binaphthyl and an inorganic base such as 1 to 3 time molar amount of cesium carbonate at room temperature or at 40° to 100° for 1 to 24 hours.

The substituting position of trifluoromesylate in the formula (7-2b) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta position and para-position. Trifluoromesylate in the formula (7-2b) may be replaced by a mesylate or a tosylate.

The compound represented by the formula (7-2b) is obtained by allowing trifluoromethanesulfonic acid anhydride to react with a compound represented by formula (7-2c) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier.]

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 3 time molar amount of, trifluoromethanesulfonic acid anhydride (manufactured by ALDRICH CHEMICAL COMPANY) to react with the compound represented by the formula (6-1), optionally in a solvent such as THF or dichloromethane, in the presence of an equimolar or more, preferably 1 to 20 time molar amount of, a base preferably an organic base such as triethylamine, at room temperature or at 0° C. to 10° C. for 1 to 24 hours. Compounds in which the trifluoromesylate in the formula (7-2b) is replaced by a mesylate or a tosylate, are obtained by allowing mesyl chloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) or tosyl chloride (manufactured by ALDRICH CHEMICAL COMPANY), respectively, instead of the trifluoromethanesulfonic acid anhydride to react with the compound represented by the formula (6-1).

The substituting position of the hydroxyl group in the formula (7-2c) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position.

The compound represented by the formula (7-2c) is obtained by allowing Lewis acid, pyridine hydrochloride, or trimethylsilane iodide to react with a compound represented by the following formula (7-2d) below.

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier.]

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various Lewis acids, such as aluminum chloride, boron trihalide, titanium tetrachloride, and tin tetrachloride, pyridine hydrochloride, or trimethylsilane iodide to react with the compound represented by the formula (7-2d) in a solvent such as dichloromethane at 0° C. to 10° C., room temperature, or 50° C. to 150° C., for 1 to 24 hours. Preferably, the reaction is carried out, for example, by allowing a 2 to 5 time molar amount of boron trihalide, preferably boron tribromide, in a solvent such as dichloromethane at room temperature or 0° C. to 10° C. for 1 to 5 hours.

The substituting position of the methoxy group in the formula (7-2d) may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position and a para-position.

The compound represented by the formula (7-2d) is obtained by reducing a compound which is selected from the compounds represented by formula (8) below

[wherein R¹, R², R³, R⁴, and m are as mentioned earlier; and

W represents a methoxy group or a nitro group] and in which W is a methoxy group.

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various reducing agents such as sodium borohydride, sodium cyanohydride, borane, and aluminum lithium hydride, preferably sodium borohydride or borane to react with the compound represented by the formula (8) in which W is a methoxy group, in a solvent such as methanol or THF, at room temperature or while heating for 1 hour or more. In particular, it is preferable to allow a 20 to 50 time molar amount of borane to react in THF at room temperature for 1 to 5 hours.

When W in the formula (8) is a methoxy group, the substituting position may be any one of an ortho-position, a meta-position, and a para-position, preferably a para-position. When W is a nitro group, the substituting position is a meta-position.

Among the compounds represented by the formula (6-1), a compound of which the substituting position of the primary amino group is the meta-position is also obtained by reducing a compound represented by the following formula (7-1) below.

[wherein R¹, R², R³, R⁴³, and m are as mentioned earlier.]

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various reducing agents such as sodium borohydride, sodium cyanohydride, borane, or lithium aluminum hydride, preferably sodium borohydride or borane to react with the compound represented by the formula (7-1) in a solvent such as methanol or THF at room temperature or while heating for 1 hour or more. In particular, it is preferable to allow a 20 to 50 time molar amount of borane to react in THF at room temperature for 1 to 5 hours.

The compound represented by the formula (7-1) is obtained by reducing a compound represented by the formula (8) in which W is a nitro group at the meta-position.

The reaction is carried out, for example, by addition of hydrogen gas to the compound represented by the formula (8) in which W is a nitro group at the meta-position in a solvent such as methanol, ethyl acetate or 1,4-dioxane in the presence of 1 mole % to 30 mole % of a catalytic reduction catalyst at room temperature or at 40° C. to 100° C. for 1 to 24 hours. Examples of preferable catalytic reduction catalyst include palladium and platinum.

To obtain the compound represented by formula (8), a compound represented by the following formula (10-1)

[wherein R¹, R², m, and W are as mentioned earlier and L³ represents a halogen] is allowed to react with a compound represented by the following formula (9)

[wherein R³ and R⁴ are as mentioned earlier].

The reaction is carried out, for example, by allowing an excess amount, preferably a 10 to 50 time molar amount of the compound represented by the formula (9) to react with the compound represented by the formula (10-1), optionally in a solvent such as THF, dioxane, or methanol, at 50° C. to 150° C., for 5 to 72 hours.

Examples of the halogen represented by L³ in the formula (10-1) include F, Cl, Br, and I, preferably F and Cl, with F being most preferable. L³ may substitute at any one of the 6- to 9-positions. It is preferable that either the 7-position or the 9-position is mono-substituted or the 7- and 9-positions are di-substituted with L³. It is more preferable that the 7-position is mono-substituted with L³.

Examples of the compounds represented by the formula (9) include dimethylamine, diethylamine, and ethylmethylamine (all the three compounds are manufactured by ALDRICH CHEMICAL COMPANY).

Among the compounds represented by formula (10-1), a compound in which W is a methoxy group is obtained by oxidizing a compound represented by formula (11) below.

[wherein R¹, R², L³, m, and W′ are as mentioned earlier; and W′ represents a methoxy group or a hydrogen atom.]

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various oxidizing agents such as hydrogen peroxide, metachloroperbenzoic acid and oxone, or an equimolar amount or more of sodium periodate in the presence of a catalytic amount of ruthenium trichloride, to react with the compound represented by the formula (11) in which W′ is a methoxy group in a solvent such as trifluoroacetic acid, dichloromethane, methanol, acetonitrile or water under ice cooling or at room temperature for 1 hour or more. In particular, it is preferable to allow a 2 to 5 time molar amount of sodium periodate to react in a dichloromethane-acetonitrile-water mixed solvent, in the presence of a 0.05 to 0.2 time molar amount of ruthenium trichloride at room temperature for 5 to 48 hours.

When W′ in the formula (11) is a methoxy group, the substituting position may be any one of an ortho-position, a meta-position, and a para-position, preferably a meta-position or a para-position.

Among the compounds represented by the formula (10-1), a compound in which W is a nitro group is obtained by nitration of a compound represented by formula (10-2) below.

[wherein R¹, R², L³, and m are as explained earlier.]

The reaction is carried out, for example, by allowing an excess molar amount of nitric acid and sulfuric acid, preferably a 10 to 40 time molar amount of fuming nitric acid and a 10 to 20 time molar amount of concentrated sulfuric acid, to react with the compound represented by the formula (10-2) at 0° C. to 10° C. or at room temperature, for 30 minutes to 3 hours.

The compound represented by the formula (10-2) is obtained by oxidizing the compound represented by the formula (11) in which W′ is a hydrogen atom.

The reaction is carried out, for example, by allowing an equimolar amount or more of any one of various oxidizing agents such as hydrogen peroxide, metachloroperbenzoic acid, or oxone, or an equimolar amount or more of sodium periodate in the presence of a catalytic amount of ruthenium trichloride, to react with the compound of the formula (11) in which W′ is a hydrogen atom, in a solvent such as trifluoroacetic acid, dichloromethane, methanol, acetonitrile, or water, under ice cooling or at room temperature for 1 hour or more. In particular, it is preferable to allow a 2 to 5 time molar amount of sodium periodate to react in a dichloromethane-acetonitrile-water mixed solvent, in the presence of a 0.05 to 0.2 time molar amount of ruthenium trichloride at room temperature for 5 to 48 hours.

The compound represented by the formula (11) is obtained by dehydrating a compound represented by formula (12) below

[wherein R¹, R², L³, m, and W′ are as mentioned earlier.] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, in a solvent such as 2,6-lutidine, toluene, or xylene in the presence of a 0.1 to 1 time molar amount of an acid such as hydrochloric acid, toluenesulfonic acid, or camphorsulfonic acid, preferably toluenesulfonic acid, at 100° C. to 150° C. for 10 to 36 hours.

To obtain the compound represented by formula (12), a compound represented by the following formula (14)

[wherein L³, m, and W′ are as mentioned earlier.] is allowed to react with a compound represented by the following formula (13)

[wherein R¹ and R² are as mentioned earlier.] according to the method described in document WO93/16055.

The reaction is carried out, for example, by allowing an equimolar amount of the compound represented by the formula (13) to react with the compound represented by the formula (14) in a solvent such as a butyl acetate-water mixed solvent, in the presence of an excess amount, preferably 3 to 5 time molar amount of inorganic base such as sodium hydroxide at 60° C. to 100° C. for 1 to 5 hours.

The compound represented by the formula (14) is obtained by allowing a base to react with a compound represented by formula (15-1) below

[wherein L³, m, and W′ are as mentioned earlier; and L⁴ represents a halogen] according to the method described in literature (see WO/16055).

The reaction is carried out, for example, by allowing to react an excess amount, preferably a 3 to 10 time molar amount of an inorganic base such as potassium hydroxide to react with the compound represented by the formula (15-1), in a solvent such as methanol, THF, or dioxane, at 50° C. to 100° C. for 1 to 24 hours.

Among the compounds represented by the formula (14), a compound in which W′ is a hydrogen atom is also obtained by allowing a metal sulfide compound to react with a compound represented by formula (15-2) below.

[wherein L³ and m are as mentioned earlier; and L⁴ represents a halogen].

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 1.5 time molar amount of a metal sulfide compound such as lithium sulfide or sodium sulfide to react with the compound represented by the formula (15-2) in a solvent such as dimethyl sulfoxide (hereinafter, “DMSO” for short) or DMF at 100° C. to 150° C. for 1 to 5 hours.

Examples of halogen represented by L⁴ in the formula (15-2) include F, Cl, Br, and 1, preferably F and Cl, with F being most preferable. L³ and L⁴ may be different; however, it is preferable that L³ and L⁴ are the same.

The compound represented by the formula (15-1) is obtained by heat treatment of a compound represented by formula (16) below

[wherein L³, m, and W′ are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by heat treatment, optionally in a solvent such as tetradecane or diphenyl ether, at 200° C. to 300° C. for 1 to 24 hours.

The compound represented by the formula (16) is obtained by allowing N,N-dimethylthiocarbamoyl chloride to react with a compound represented by formula (17) below

[wherein L³, m, and W′ are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably a 1 to 1.5 time molar amount of N, N-dimethylthiocarbamoyl chloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.) to react with the compound represented by the formula (16), in a solvent such as THF or dioxane, in the presence of an excess amount, preferably a 1.5 to 3 time molar amount of an organic base such as triethylamine, and a catalytic amount, preferably a 0.1 to 0.2 time molar amount of a strong organic base such as dimethylaminopyridine, or an equimolar amount or more, preferably a 1 to 1.5 time molar amount of an inorganic base such as sodium hydride at room temperature or at 50° C. to 100° C. for 1 to 24 hours.

To obtain the compound represented by formula (17), a compound represented by the following formula (19)

[wherein L³ and m are as mentioned earlier] is allowed to react with a compound in the following formula (18) according to the method described in literature (see Chemistry Letters, 823-824, 1996).

[wherein W′ is as mentioned earlier.]

The reaction is carried out, for example, by allowing a 2 time molar amount of the compound represented by the formula (18) to react with the compound represented by the formula (19), in a solvent such as DMF, in the presence of a 0.05 time molar amount of palladium chloride, a 0.2 time molar amount of lithium chloride, and a 2 time molar amount of sodium carbonate at 100° C. to 150° C. for 1 to 24 hours.

Examples of the compounds represented by the formula (18) include 4-iodoanisole, 3-iodoanisole, and iodobenzene (all the three are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.).

Examples of the compound represented by the formula (19) include 5-fluorosalicyl aldehyde (manufactured by APOLLO CHEMICAL COMPANY LTD.), and 3-fluorosalicyl aldehyde (manufactured by ALDRICH CHEMICAL COMPANY).

Furthermore, the compound represented by the formula (17) is also obtained by allowing a Lewis acid to react with a compound represented by formula (20) below

[wherein L³, m, and W′ are as mentioned earlier] according to the method described in literature (Journal of Compounds and Radiopharmaceuticals, Vol. 34, 643-652, 1994).

The reaction is carried out, for example, by allowing an excess amount, preferably a 1.5 to 5 time molar amount, of a Lewis acid, preferably titanium tetrachloride or aluminum chloride, more preferably titanium tetrachloride to react with the compound represented by the formula (20), optionally in a solvent such as nitrobenzene at 120° C. to 160° C., for 1 to 24 hours.

The compound represented by the formula (20) is obtained by allowing a compound represented by formula (21) below

[wherein L³ and m are as mentioned earlier] to react with a compound represented by formula (22) below

[wherein W′ is as mentioned earlier] according to the method described in literature (see Journal of Compounds and Radiopharmaceuticals, Vol. 34, 643-652, 1994).

The reaction is carried out, for example, by allowing an equimolar amount of the compound represented by the formula (22) to react with the compound represented by the formula (21), in a solvent such as dichloromethane, chloroform or THF, in the presence of an equimolar amount, preferably a 1 to 1.5 time molar amount of an organic base such as triethylamine at 40° C. to 60° C. for 1 to 5 hours.

Examples of the compounds represented by the formula (21) include 4-fluorophenol, 2-fluorophenol, and 2,4-difluorophenol (all the three are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.).

Examples of the compounds represented by the formula (22) include 4-methoxybenzoyl chloride, 3-methoxybenzoyl chloride, and benzoyl chloride (all the three are manufactured by ALDRICH CHEMICAL COMPANY).

The compound represented by the formula (13) is obtained by allowing chlorosulfonic acid to react with a compound represented by formula (23) below

[wherein R¹ and R² are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 2 time molar amount of chlorosulfonic acid to react with the compound represented by the formula (23), in a solvent such as dichloromethane at 0° to 10° C. or room temperature for 1 to 24 hours.

The compound represented by the formula (23) is obtained by reducing a compound represented by formula (24) below

[wherein R¹ and R² are as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an excess molar amount, preferably a 1.5 to 3 time molar amount of lithium aluminum hydride to react with the compound represented by the formula (23), in a solvent such as THF at room temperature or at 50° C. to 60° C. for 1 to 5 hours.

The compound represented by the formula (24) is obtained by hydrolyzing, with an acid, of a compound represented by formula (25) below

[wherein R¹ and R² are as mentioned earlier] according to the method described in literature (see WO/16055).

The reaction is carried out, for example, by allowing an excess amount, preferably a 30 to 300 time molar amount of an acid, preferably 1 N to 5 N hydrochloric acid, to react with the compound represented by the formula (25), optionally in a solvent such as THF or methanol, at room temperature for 1 to 24 hours.

The compound represented by the formula (25) is obtained by allowing a base to react with a compound represented by formula (26) below

[wherein R¹ is as mentioned earlier] and then allowing a compound represented by formula (27) below [Chemical Formula 74] R²—L⁵  (27) [wherein R² is as mentioned earlier; and L⁵ represents a halogen] to react with the resultant according to the method described in literature (WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 1.5 time molar amount of an inorganic base such as sodium hydride to react with the compound represented by the formula (26), in a solvent such as DMF, at 0° C. to 10° C. or room temperature for 1 to 3 hours and then allowing an equimolar amount or more, preferably 1 to 1.5 time molar amount of the compound represented by the formula (27) at 0° C. to 10° C. or room temperature for 1 to 24 hours.

Examples of the halogen represented by L⁵ in the formula (27) include F, Cl, Br, and I, preferably Br and I, with I being most preferable.

Examples of the compounds represented by the formula (27) include iodoethane, 1-iodopropane, 1-iodobutane, 1-iodopentane, and 1-iodohexane (all are manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.).

The compound represented by the formula (26) is obtained by allowing benzaldehyde to react with a compound represented by formula (28) below

[wherein R¹ is as mentioned earlier] according to the method described in literature (see WO93/16055).

The reaction is carried out, for example, by allowing an equimolar amount or more, preferably 1 to 1.2 time molar amount of benzaldehyde (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) to react with the compound represented by the formula (28) in the presence of an excess amount, preferably 2 to 3 time molar amount of an organic base such as triethylamine and-an excess amount, preferably a 1.5 to 2 time molar amount of a dehydrating agent such as anhydrous magnesium sulfate in a solvent such as dichloromethane at room temperature for 1 to 24 hours.

Examples of the compound represented by the formula (28) include methyl 2-aminobutyrate hydrochloride (manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.), methyl 2-aminohexanoate hydrochloride (manufactured by BACHEM CHEMICAL COMPANY), methyl 2-aminopentanoate hydrochloride (prepared by allowing thionyl chloride to react with norvaline manufactured by TOKYO CHEMICAL INDUSTRIES, LTD. in methanol according to the method described in WO93/16055), methyl 2-aminoheptanoate hydrochloride, (prepared similarly from 2-aminoheptanoic acid manufactured by FLUKA CHEMICAL CORPORATION), and methyl 2-aminooctanoate hydrochloride (prepared similarly from 2-aminocaprylic acid manufactured by TOKYO CHEMICAL INDUSTRIES, LTD.).

The compounds represented by the formula (1) can have a plurality of stereoisomers depending on the number of asymmetric centers. Those isomers that are in a relationship of diastereomers thereto can be separated by silica gel column chromatography or fractionating crystallization during the synthesis of any one of the compounds represented by the formulae (1), (3), (4-1), (4-2), (6-1), (6-2), and from (7-2a) to (7-2d). Further, those isomers that are in a relationship of enantiomers thereto can be separated by column chromatography that uses an optically active carrier or separated by silica gel column chromatography or fractionating crystallization after they are derived to diastereomers, during the synthesis of any one of the compounds represented by the formulae (1), (3), (4-1), (4-2), (6-1), (6-2), and from (7-2a) to (7-2d). On the other hand, geometric isomers can be separated by silica gel column chromatography or fractionating crystallization during the synthesis of any one of the compounds represented by the formulae (1), (3), (4-1), and (4-2).

The compounds represented by the formula (1) of the present invention include the acid addition salts. The acid addition salts are preferably pharmaceutically acceptable ones, which include, for example, various types of known salts, such as hydrochlorides, hydrobromides, sulfates, hydrogen sulfates, dihydrogen phosphates, citrates, maleates, tartarates, fumarates, gluconates, and methanesulfonate. When acid addition salts are to be made, addition of an equimolar amount or a few time molar amount of an acid component to the compounds represented by the formula (1) can provide acid addition salts thereof. Examples of the acid component that can be used include pharmaceutically acceptable mineral acids or organic acids, such as hydrochloric acid, hydrobromic acid, sulfuric acid, hydrogen sulfuric acid, dihydrogen phosphoric acid, citric acid, maleic acid, tartaric acid, fumaric acid, gluconic acid, and methanesulfonic acid.

The compounds of the present invention have ileal bile acid transporter inhibiting activities and have blood cholesterol lowering effects, and ameliorating effects for cholestasis-accompanying hepatopathy. Therefore, it has been verified that the compounds of the present invention can be used as cholesterol lowering agents and as ameliorating agents for cholestasis-accompanying hepatopathy. No case of death has been observed when the compounds of the present invention were orally administered to rats in a dosage of 3 mg per kg of body weight twice a day for 3.5 days. Furthermore, the compounds of the present invention showed no microbe mutagenicity, which indicates that the compounds of the present invention can be used safely.

Specific examples of the cholesterol lowering agent include pharmaceutical compositions for the treatment and prevention of any one of hyperlipidemia, arteriosclerosis, and syndrome X. Detailed explanation of these disorders is as follows.

That is, examples of hyperlipidemia include hyperchylomicronemia, low density lipoprotein (LDL) hyperlipoproteinemia, familial hypercholesterolemia, very low density lipoprotein (VLDL) hyperlipoproteinemia, hypertriglyceridemia, and disorders resulting from combinations of these. Atheriosclerosis may be mentioned as a preferable example of target arteriosclerosis that is subjected to treatment and prevention in the present invention. Syndrome X, as explained earlier, is a disorder that sometimes is one of the causes of hyperlipidemia and sometimes causes arteriosclerosis eventually.

The compounds of the present invention and pharmaceutical compositions containing the same are also useful as drugs for the treatment and prevention of cholestasis-accompanying hepatopathy and are particularly useful as drugs for the treatment and prevention of primary biliary cirrhosis and primary sclerosing cholangitis. Cholestasis means a state where eventually bile is not excreted from liver to duodenum for some reason. Once cholestasis occurs, it causes liver disorder, which is called as cholestasis-accompanying hepatopathy. Specific examples of hepatopathy caused by cholestasis include primary biliary cirrhosis, primary sclerosing cholangitis, and cholestatic hepatitis (cholangiolitic hepatitis) (Medical Encyclopedia published by Nanzando, 1333-1334). Direct causes of cholestasis may include gallstones, etc. developed in bile duct or gall bladder. Primary biliary cirrhosis and primary sclerosing cholangitis are disorders that are not caused directly by gallstones.

The compounds of the present invention and pharmaceutical compositions containing the same are also useful as drugs for the treatment and prevention of obesity and fatty liver. Obesity means a state where fat is excessively accumulated in the body and specifically means a Body Mass Index (BMI) of more than 26 (Yoshio Ikeda et al., Nippon Rinsho (Japan Clinical), 53:229-236, 1995). Fatty liver means a state where usually, neutral fat is accumulated in large quantities in liver; in general, liver in which fat droplets are accumulated in approximately 30% or more of hepatic lobules is defined as fatty liver (Kyoichiro Tojima et al., Nippon Rinsho (Japan Clinical), 53: 354-358, 1995).

Upon manufacturing drugs of the present invention, it is preferable to make a pharmaceutical composition by optionally adding a pharmaceutically acceptable carrier to an effective amount of the compound represented by the formula (1) or its salts. Examples of the pharmaceutically acceptable carriers include an excipient, a binder such as carboxymethyl cellulose, a disintegrating agent, a lubricant, and an additive. The compounds of the present invention can be administered orally to humans in the form of a tablet, a powder, a granule, a capsule, a sugar coated tablet, a liquid, a syrup and so forth. Dosages may vary according to the age, weight, and symptom of a patient. Normally, in the case of an adult, a dosage of 0.1 mg to 500 mg is administered once a day or in a plural of times a day in portions. Administration period is as follows. Generally, the drug is administered everyday for a few weeks to a few months. However, the dosage and the administration period of the drug may be increased or decreased according to the symptom of the patient.

EXAMPLES

The present invention is further explained based on the following examples. However, the present invention is not restricted to the following examples. Thin layer chromatography (TLC) was performed using Precoated Silica Gel 60 F254 (manufactured by MERCK COMPANY) and spots were confirmed by UV (254 nm) irradiation. Measurement of nuclear magnetic resonance spectra (NMR) was carried out with AL-300 (FT-NMR, manufactured by JEOL COMPANY). Chemical shifts were indicated by δ (ppm) by use of tetramethylsilane (TMS) as an internal standard. Mass spectrum (MS) was measured by use of JMS-SX102 (manufactured by JEOL COMPANY) using fast atom bombardment mass spectrum (FAB-MS). Silica gel 60 of from 230 mesh to 400 mesh (manufactured by MERCK COMPANY) was used as a filler for silica gel column. In the operations carried out in the examples, “filtration” means filtration carried out by using a Kiriyama funnel and filter paper for the funnel (both the funnel and the filter paper are manufactured by NIPPON RIGAKU KIKAI CO., LTD.) and “concentration” means removal by evaporation of solvent or excess reagent under reduced pressure by using an evaporator (manufactured by TOKYO RIGAKU KIKAI CO., LTD.)

Example 1 1-{5-[3-(3,3-Dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane Bromide

Step a: Synthesis of methyl 2-benzylideneaminohexanoate

To a suspension of 7.79 g of methyl 2-aminohexanoate hydrochloride in 70 ml of dichloromethane were added 8.67 g of triethylamine (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), 7.74 g of anhydrous magnesium sulfate, and 4.55 g of benzaldehyde and the resultant was stirred overnight at room temperature. The reaction suspension was then filtered and the filtrate was concentrated. 280 ml of ether was added to the residue and the resultant suspension was filtered and the filtrate was concentrated. Again, 280 ml of ether was added to the residue and filtration and concentration were similarly repeated to obtain 10.0 g of the title compound.

Step b: Synthesis of methyl 2-benzylideneamino-2-butylhexanoate

To a solution of 8.06 g of the compound obtained in the step a in 25 ml of DMF was added 1.66 g of sodium hydride (60% dispersion in oil) (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) in an argon atmosphere under ice cooling, and the resultant was stirred for 2 hours at room temperature. To the reaction suspension was dropwise added a solution of 8.90 g of 1-iodobutane in 15 ml of DMF in argon atmosphere under ice cooling, and the mixture was stirred at room temperature for 3 hours. Under ice cooling, a solution of 5.5 g of ammonium chloride in 50 ml of water was dropwise added to the reaction suspension and then the mixture was separated by adding to it 80 ml of ether and 30 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 10.0 g of the title compound.

Step c: Synthesis of methyl 2-amino-2-butylhexanoate

To a solution of 15.46 g of the compound obtained in the step b in 70 ml of petroleum ether was added 30 ml of 1 N hydrochloric acid, and the mixture was stirred for 1 hour at room temperature. The reaction solution was separated by adding to it 60 ml of water. The water layer was washed twice with 80 ml of ether, an aqueous solution of 5N sodium hydroxide was added to it, and pH of the solution was adjusted to from 9 to 10. The water layer was separated by adding to it 160 ml of ethyl acetate and the organic layer was washed with 160 ml of saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 10.0 g of the title compound.

Step d: Synthesis of 2-amino-2-butylhexanol

To a suspension of 7.52 g of lithium aluminum hydride (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) in 50 ml of THF was dropwise added a solution of 17.34 g of the compound obtained in the step c in 120 ml of THF under ice cooling and the mixture was stirred at 60° C. for 1 hour. To the reaction suspension was dropwise added 25 ml of water under ice cooling. Then, 600 ml of ethyl acetate was added to the resultant at room temperature. The mixture was filtered through Celite and washed with 900 ml of ethyl acetate. The filtrate was concentrated to obtain 10.0 g of the title compound.

Step e: Synthesis of 2-amino-2-butylhexyl hydrogen sulfate

To a solution of 7.97 g of the compound obtained in the step d in 90 ml of dichloromethane was dropwise added 8.04 g of chlorosulfonic acid under ice cooling and the mixture was stirred overnight at room temperature. The reaction solution was concentrated and 90 ml of acetone-ether (1:1) was added to the residue. The mixture was allowed to stand at −20° C. for 3 hours. The precipitation was filtered, washed with 300 ml of acetone-ether (1:1) to obtain 10.0 g of the title compound.

Step f: Synthesis of 4-fluoro-2-benzoylthiophenol

To a solution of 10.1 g of 2,5-difluorobenzophenone in 200 ml of DMSO was added 3.5 g of lithium sulfide (manufactured by ALDRICH CHEMICAL COMPANY) and the mixture was stirred in a nitrogen atmosphere at 120° C. for 3 hours. To the reaction solution was added 200 ml of 1 N hydrochloric acid under ice cooling, and further 400 ml of ethyl acetate and 200 ml of water were added to the mixture to separate it. The organic layer was washed with 400 ml of water and then with 200 ml of saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain 10.54 g of the title compound.

Step g: Synthesis of 2-(2-amino-2-butylhexylthio)-5-fluoro-benzophenone

To a solution of 10.54 g of the compound obtained in the step f in 100 ml of butyl acetate were added 11.50 g of the compound obtained in the step e and a solution of 7.25 g of sodium hydroxide in 100 ml of water and the mixture was stirred at 90° C. for 1 hour. The reaction mixture was separated by adding to it 300 ml of ethyl acetate and 300 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with chloroform-methanol-28% aqueous ammonia (50:1:0.1) to obtain 10.09 g of the title compound.

Step h: Synthesis of 3,3-dibutyl-2,3-dihydro-7-fluoro-5-phenyl-1,4-benzothiazepine

To a solution of 10.08 g of the compound obtained in the step g in 40 ml of 2,6-lutidine (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) was added 0.60 g of toluenesulfonic acid monohydrate (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), and the mixture was stirred at 130° C. for 34 hours. The reaction solution was separated by adding to it 400 ml of ethyl acetate and 400 ml of water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (30:1) to obtain 7.87 g of the title compound.

Step i: Synthesis of 3,3-dibutyl-2,3-dihydro-7-fluoro-5-phenyl-1,4-benzothiazepine-1,1-dioxide

To a solution of 7.86 g of the compound obtained in the step h in 50 ml of dichloromethane were added 150 ml of acetonitrile, a solution of 13.3 g of sodium periodate (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.) in 70 ml of water, and 0.42 g of ruthenium trichloride (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), and the mixture was stirred at room temperature for 24 hours. The reaction suspension was separated by adding to it 300 ml of dichloromethane and 300 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (6:1) to obtain 5.72 g of the title compound.

Step j: Synthesis of 3,3-dibutyl-2,3-dihydro-7-fluoro-5-(3-nitrophenyl)-1,4-benzothiazepine-1,1-dioxide

To 5.32 g of the compound obtained in the step i was added a mixed solution composed of 20 ml of fuming nitric acid and 15 ml of concentrated sulfuric acid under ice cooling and the mixture was stirred at room temperature for 1 hour. The reaction mixture was dropwise added to a 5N sodium hydroxide solution under ice cooling, and the mixture was separated by adding to it 150 ml of dichloromethane and 50 ml of water at room temperature. The organic layer was washed with 150 ml of saturated saline, dried over anhydrous sodium sulfate, and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (5:1) to obtain 5.48 g of the title compound.

Step k: Synthesis of 3,3-dibutyl-2,3-dihydro-7-dimethylamino-5-(3-nitrophenyl)-1,4-benzothiazepine-1,1-dioxide

To 5.48 g of the compound obtained in the step j was added 200 ml of a THF solution of 2 mol/l dimethylamine (manufactured by ALDRICH CHEMICAL COMPANY) and the mixture was heated at 55° C. for 14 hours. The reaction solution was concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (2:1). The eluate was washed with 50 ml of ether to obtain 5.69 g of the title compound.

Step I: Synthesis of 3,3-dibutyl-2,3-dihydro-7-dimethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

To a solution of 5.9 g of the compound obtained in the step k in 100 ml of chloroform were added 100 ml of methanol and 1.2 g of 10% palladium-carbon (manufactured by MERCK COMPANY), and the mixture was stirred in a hydrogen atmosphere at room temperature for 4 hours. The catalyst in the reaction suspension was removed by filtering and the filtrate was concentrated. The residue was charged in a silica gel column and then eluted with chloroform-methanol (30:1) to obtain 4.38 g of the title compound.

Step m: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-dimethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

To 4.38 g of the compound obtained in the step I was added 150 ml of a THF solution of 1 mol/l borane-THF complex (manufactured by KANTO CHEMICAL COMPANY), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was dropwise added 10 ml of water under ice cooling until foaming stopped and then the reaction solution was stirred at room temperature for 1.5 hours. The mixture was then separated by adding-to it 150 ml of ethyl acetate, 50 ml of water, and 100 ml of aqueous solution of 1N sodium hydroxide at room temperature. The organic layer was washed with 150 ml of water and allowed to stand at room temperature for 1.5 hours. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (1:1) to obtain 3.83 g of the title compound.

Step n: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-dimethylamino-5-[3-(6-bromohexanoyl)aminophenyl]-1,4-benzothiazepine-1,1-dioxide

To a solution of 0.73 g of the compound obtained in the step m in 15 ml of dichloromethane was added 0.27 g of potassium carbonate and then 0.37 g of 6-bromo-n-caproyl chloride, and the mixture was stirred at room temperature for 20 minutes. The reaction solution was separated by adding to it 35 ml of dichloromethane and 50 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (1:1) to obtain 1.00 g of the title compound.

Step o: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-dimethylamino-5-[3-(6-bromothiohexanoyl)aminophenyl]-1,4-benzothiazepine-1,1-dioxide

To a solution of 50 mg of the compound obtained in the step n in 1.5 ml of THF was added 90 mg of Lawesson's reagent, and the mixture was stirred at room temperature for 40 hours. The reaction solution was then separated by adding to it 6 ml of ethyl acetate and 8 ml of water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was charged in a silica gel column and eluted with hexane-ethyl acetate (2:1) to obtain 37 mg of the title compound. Rf value 0.41 (developed with hexane:ethyl acetate=3:1).

Step p: Synthesis of 1-{5-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]-pentyl}-1-azoniabicyclo[2.2.2]octane Bromide

To a solution of 36 mg of the compound obtained in the step o in 1 ml of acetonitrile was added 7 mg of quinuclidine (ta-287 mentioned earlier), and the mixture was heated at 50° C. for 22 hours. The reaction solution was concentrated and the residue was dissolved in 0.2 ml of dichloromethane. 2 ml of ether was added to the solution and the precipitate formed was washed with 2 ml of ether to obtain 32 mg of the title compound. ¹H-NMR (CDCl₃) δ: 0.84 (3H, t); 0.90 (3H, t); 1.18-1.51 (8H, m); 1.60-2.23 (17H, m); 2.84 (6H, s); 2.95-3.12 (3H, m); 3.26-3.43 (3H, m); 3.58 (6H, t); 6.03-6.07 (2H, m); 6.47 (1H, dd); 7.34-7.39 (2H, m); 7.72-7.76 (1H, m); 7.84 (1H, d); 7.98 (1H, s); 11.56 (1H, s).

MS (m/z): 667 (M+).

Example 2 1-{5-[3-(3-butyl-3-ethyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo-[2.2.2]octane Bromide

Step a: Synthesis of 3-butyl-3-ethyl-2,3,4,5-tetrahydro-7-dimethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that methyl 2-aminobutyrate hydrochloride instead of the methyl 2-aminohexanoate hydrochloride was used in the step a of Example 1 to obtain the title compound.

Step b: Synthesis of 1-{5-[3-(3-butyl-3-ethyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo [2.2.2]octane Bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step a in this example was used to obtain the title compound.

Example 3 1-{5-[3-(3,3-dipropyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo-[2.2.2]-octane Bromide

Step a: Synthesis of 3,3-dipropyl-2,3,4,5-tetrahydro-7-dimethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps d to m in Example 1 was followed except that 2-amino-2-propylpentanoic acid (manufactured by ADVANCED CHEMTECH COMPANY) was used instead of the compound obtained in the step c in Example 1 to obtain the title compound.

Step b: Synthesis of 1-{5-[3-(3,3-dipropyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step a in this example was used to obtain the title compound.

Example 4 1-{5-[3-(3,3-dipentyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]-pentyl}-1-azoniabicyclo[2.2.2]octane bromide

Step a: Synthesis of Methyl 2-aminoheptanoate Hydrochloride

To a suspension of 2.18 g of 2-aminoheptanoic acid in 50 ml of methanol was dropwise added 2.19 g of thionyl chloride (manufactured by WAKO PURE CHEMICAL INDUSTRIES LTD.), and the mixture was stirred overnight at 60° C. Methanol and thionyl chloride were removed by evaporation and the residue was washed with 20 ml of ether to obtain 2.84 g of the title compound.

Step b: Synthesis of 3,3-dipentyl-2,3,4,5-tetrahydro-7-dimethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that the compound obtained in the step a in this example was used and that in the step b, 1-iodopentane instead of 1-iodobutane was allowed to react to obtain the title compound.

Step c: Synthesis of 1-{5-[3-(3,3-dipentyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step b in this example was used to obtain the title compound.

Example 5 1-{5-[3-(3,3-dihexyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane Bromide

Step a: Synthesis of Methyl 2-aminooctanoate Hydrochloride

Instead of 2-aminoheptanoic acid obtained in the step a in Example 4, 2-aminocaprylic acid was used to obtain the title compound.

Step b: Synthesis of 3,3-dihexyl-2,3,4,5-tetrahydro-7-dimethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that the compound obtained in the step a in this example was used and that in the step b, 1-iodohexane instead of 1-iodobutane was allowed to react to obtain the title compound.

Step c: Synthesis of 1-{5-[3-(3,3-dihexyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo-[2.2.2]octane Bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step b in this example was used to obtain the title compound.

Example 6 1-{5-[3-(3,3-dibutyl-7-diethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane Bromide

Step a: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-diethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that in the step k, diethylamine instead of dimethylamine was allowed to react to obtain the title compound.

Step b: Synthesis of 1-{5-[3-(3,3-dibutyl-7-diethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl}-1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step a in this example was used to obtain the title compound.

Example 7 1-{5-[3-(3,3-dibutyl-7-ethylmethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane Bromide

Step a: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-ethylmethyl-amino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide

The procedure in the steps a to m in Example 1 was followed except that in the step k, ethylmethylamine instead of dimethylamine was allowed to react to obtain the title compound.

Step b: Synthesis of 1-{5-[3-(3,3-dibutyl-7-ethylmethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]pentyl}—1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the steps n to p in Example 1 was followed except that the compound obtained in the step a in this example was used to obtain the title compound.

Example 8 1-{5-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]-pentyl}-1-azoniabicyclo[2.2.2]octane Bromide (an Optically Active Form)

Step a: Synthesis of 3,3-dibutyl-2,3,4,5-tetrahydro-7-dimethylamino-5-(3-aminophenyl)-1,4-benzothiazepine-1,1-dioxide (an Optically Active Form)

The compound obtained in the step m in Example 1 was charged in an optical column CHIRALCEL-OJ for preparatory chromatography (manufactured by DAICEL CHEMICAL INDUSTRIES LTD., having a particle size of 10 μm, a diameter of 2 cm, and a length of 25 cm) at a flow rate of 18.9 ml/min, and then eluted with methanol, to separate the compounds into compounds of S form and R form. The retention times of the obtained optically active forms in the optical column for analysis were 7 minutes and 14 minutes, respectively. Column; CHIRALPAK-OJ (manufactured by DAICEL CHEMICAL INDUSTRIES LTD., having a particle size of 10 μm, a diameter of 0.46 cm, and a length of 25 cm), mobile phase; methanol, flow rate; 0.5 ml/min, UV wavelength detected; 288 nm.

Step b: Synthesis of 1-{5-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]-pentyl}-1-azoniabicyclo[2.2.2]octane bromide (an Optically Active Form) The procedure in the steps n to p in Example 1 was followed except that the optically active synthetic intermediate obtained in the step a in this example was used to obtain the title compound.

Example 9 1-(3-{3-[3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}-propyl)-1-azoniabicyclo[2.2.2]octane Bromide

Step a: Synthesis of 1-(3-isothiocyanatopropyl)-1-azoniabicyclo-[2.2.2]octane bromide

To a solution of 55 mg of 3-bromopropyl isothiocyanate in 1 ml of acetonitrile was added 33 mg of quinuclidine, and the mixture was heated at 50° C. for 19 hours. The reaction solution was concentrated and the residue was washed 3 times with 1 ml of ether to obtain the title compound.

Step b: Synthesis of. 1-(3-{3-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1-azoniabicyclo[2.2.2]octane Bromide

To a solution of 60 mg of the compound obtained in the step m in Example 1 in 1.5 ml of chloroform was added 0.5 ml of a solution of 43 mg of the compound obtained in the step a in this example in 0.5 ml of acetonitrile, and the mixture was heated at 55° C. overnight. The reaction solution was concentrated and the residue was dissolved in 0.3 ml of dichloromethane. To the resultant was added 1.5 ml of ether, and the precipitate formed was washed with 2 ml of ether to obtain 77 mg of the title compound. MS (m/z): 654 (M+).

Example 10 1-(3-{3-[3-(3-butyl-3-ethyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl] thioureido}propyl)-1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 2 was used to obtain the title compound.

[Example 11 1-(3-{3-[3-(3,3-dipropyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido)-1-azoniabicyclo[2.2.2]octane bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 3 was used to obtain the title compound.

Example 12 1-(3-{3-[3-(3,3-dipentyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step b in Example 4 was used to obtain the title compound.

Example 13 1-(3-{3-[3-(3,3-dihexyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step b in Example 5 was used to obtain the title compound.

Example 14 1-(3-{3-[3-(3,3-dibutyl-7-diethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 6 was used to obtain the title compound.

Example 15 1-(3-{3-[3-(3,3-dibutyl-7-ethylmethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1-azoniabicyclo[2.2.2]octane Bromide

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 7 was used to obtain the title compound.

Example 16 1-(3-{3-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}propyl)-1-azoniabicyclo[2.2.2]octane Bromide (an Optically Active Form)

The procedure in the step b in Example 9 was followed except that instead of the compound obtained in the step m in Example 1, the compound obtained in the step a in Example 8 was used to obtain the title compound.

Examples 17 to 3785

As shown in the following formulae,

the procedures in the steps a and b in Example 9 are followed except that any one of the various isothiocyanate (is-1) to (is-14) represented by the formula (5-2b), any one of various tertiary amines (ta-1) to (ta-377) represented by the formula (2), and the compound obtained in the step m in Example 1 are used to obtain compounds of Examples 17 to 3785 as represented by the formula (1A) as shown in Table 2. In the formula (1A), “-sp-” indicates any one of the (sp-1) to (sp-22) described above and “-an” indicates any one of the (an-1) to (an-377) described above. TABLE 2 Reaction Compound Example reagent of Example No. is ta sp an 17 is-1 ta-1 sp-1 an-1 18 is-1 ta-2 sp-1 an-2 19 is-1 ta-3 sp-1 an-3 20 is-1 ta-4 sp-1 an-4 21 is-1 ta-5 sp-1 an-5 22 is-1 ta-6 sp-1 an-6 23 is-1 ta-7 sp-1 an-7 24 is-1 ta-8 sp-1 an-8 25 is-1 ta-9 sp-1 an-9 26 is-1 ta-10 sp-1 an-10 27 is-1 ta-11 sp-1 an-11 28 is-1 ta-12 sp-1 an-12 29 is-1 ta-13 sp-1 an-13 30 is-1 ta-14 sp-1 an-14 31 is-1 ta-15 sp-1 an-15 32 is-1 ta-16 sp-1 an-16 33 is-1 ta-17 sp-1 an-17 34 is-1 ta-18 sp-1 an-18 35 is-1 ta-19 sp-1 an-19 36 is-1 ta-20 sp-1 an-20 37 is-1 ta-21 sp-1 an-21 38 is-1 ta-22 sp-1 an-22 39 is-1 ta-23 sp-1 an-23 40 is-1 ta-24 sp-1 an-24 41 is-1 ta-25 sp-1 an-25 42 is-1 ta-26 sp-1 an-26 43 is-1 ta-27 sp-1 an-27 44 is-1 ta-28 sp-1 an-28 45 is-1 ta-29 sp-1 an-29 46 is-1 ta-30 sp-1 an-30 47 is-1 ta-31 sp-1 an-31 48 is-1 ta-32 sp-1 an-32 49 is-1 ta-33 sp-1 an-33 50 is-1 ta-34 sp-1 an-34 51 is-1 ta-35 sp-1 an-35 52 is-1 ta-36 sp-1 an-36 53 is-1 ta-37 sp-1 an-37 54 is-1 ta-38 sp-1 an-38 55 is-1 ta-39 sp-1 an-39 56 is-1 ta-40 sp-1 an-40 57 is-1 ta-41 sp-1 an-41 58 is-1 ta-42 sp-1 an-42 59 is-1 ta-43 sp-1 an-43 60 is-1 ta-44 sp-1 an-44 61 is-1 ta-45 sp-1 an-45 62 is-1 ta-46 sp-1 an-46 63 is-1 ta-47 sp-1 an-47 64 is-1 ta-48 sp-1 an-48 65 is-1 ta-49 sp-1 an-49 66 is-1 ta-50 sp-1 an-50 67 is-1 ta-51 sp-1 an-51 68 is-1 ta-52 sp-1 an-52 69 is-1 ta-53 sp-1 an-53 70 is-1 ta-54 sp-1 an-54 71 is-1 ta-55 sp-1 an-55 72 is-1 ta-56 sp-1 an-56 73 is-1 ta-57 sp-1 an-57 74 is-1 ta-58 sp-1 an-58 75 is-1 ta-59 sp-1 an-59 76 is-1 ta-60 sp-1 an-60 77 is-1 ta-61 sp-1 an-61 78 is-1 ta-62 sp-1 an-62 79 is-1 ta-63 sp-1 an-63 80 is-1 ta-64 sp-1 an-64 81 is-1 ta-65 sp-1 an-65 82 is-1 ta-66 sp-1 an-66 83 is-1 ta-67 sp-1 an-67 84 is-1 ta-68 sp-1 an-68 85 is-1 ta-69 sp-1 an-69 86 is-1 ta-70 sp-1 an-70 87 is-1 ta-71 sp-1 an-71 88 is-1 ta-72 sp-1 an-72 89 is-1 ta-73 sp-1 an-73 90 is-1 ta-74 sp-1 an-74 91 is-1 ta-75 sp-1 an-75 92 is-1 ta-76 sp-1 an-76 93 is-1 ta-77 sp-1 an-77 94 is-1 ta-78 sp-1 an-78 95 is-1 ta-79 sp-1 an-79 96 is-1 ta-80 sp-1 an-80 97 is-1 ta-81 sp-1 an-81 98 is-1 ta-82 sp-1 an-82 99 is-1 ta-83 sp-1 an-83 100 is-1 ta-84 sp-1 an-84 101 is-1 ta-85 sp-1 an-85 102 is-1 ta-86 sp-1 an-86 103 is-1 ta-87 sp-1 an-87 104 is-1 ta-88 sp-1 an-88 105 is-1 ta-89 sp-1 an-89 106 is-1 ta-90 sp-1 an-90 107 is-1 ta-91 sp-1 an-91 108 is-1 ta-92 sp-1 an-92 109 is-1 ta-93 sp-1 an-93 110 is-1 ta-94 sp-1 an-94 111 is-1 ta-95 sp-1 an-95 112 is-1 ta-96 sp-1 an-96 113 is-1 ta-97 sp-1 an-97 114 is-1 ta-98 sp-1 an-98 115 is-1 ta-99 sp-1 an-99 116 is-1 ta-100 sp-1 an-100 117 is-1 ta-101 sp-1 an-101 118 is-1 ta-102 sp-1 an-102 119 is-1 ta-103 sp-1 an-103 120 is-1 ta-104 sp-1 an-104 121 is-1 ta-105 sp-1 an-105 122 is-1 ta-106 sp-1 an-106 123 is-1 ta-107 sp-1 an-107 124 is-1 ta-108 sp-1 an-108 125 is-1 ta-109 sp-1 an-109 126 is-1 ta-110 sp-1 an-110 127 is-1 ta-111 sp-1 an-111 128 is-1 ta-112 sp-1 an-112 129 is-1 ta-113 sp-1 an-113 130 is-1 ta-114 sp-1 an-114 131 is-1 ta-115 sp-1 an-115 132 is-1 ta-116 sp-1 an-116 133 is-1 ta-117 sp-1 an-117 134 is-1 ta-118 sp-1 an-118 135 is-1 ta-119 sp-1 an-119 136 is-1 ta-120 sp-1 an-120 137 is-1 ta-121 sp-1 an-121 138 is-1 ta-122 sp-1 an-122 139 is-1 ta-123 sp-1 an-123 140 is-1 ta-124 sp-1 an-124 141 is-1 ta-125 sp-1 an-125 142 is-1 ta-126 sp-1 an-126 143 is-1 ta-127 sp-1 an-127 144 is-1 ta-128 sp-1 an-128 145 is-1 ta-129 sp-1 an-129 146 is-1 ta-130 sp-1 an-130 147 is-1 ta-131 sp-1 an-131 148 is-1 ta-132 sp-1 an-132 149 is-1 ta-133 sp-1 an-133 150 is-1 ta-134 sp-1 an-134 151 is-1 ta-135 sp-1 an-135 152 is-1 ta-136 sp-1 an-136 153 is-1 ta-137 sp-1 an-137 154 is-1 ta-138 sp-1 an-138 155 is-1 ta-139 sp-1 an-139 156 is-1 ta-140 sp-1 an-140 157 is-1 ta-141 sp-1 an-141 158 is-1 ta-142 sp-1 an-142 159 is-1 ta-143 sp-1 an-143 160 is-1 ta-144 sp-1 an-144 161 is-1 ta-145 sp-1 an-145 162 is-1 ta-146 sp-1 an-146 163 is-1 ta-147 sp-1 an-147 164 is-1 ta-148 sp-1 an-148 165 is-1 ta-149 sp-1 an-149 166 is-1 ta-150 sp-1 an-150 167 is-1 ta-151 sp-1 an-151 168 is-1 ta-152 sp-1 an-152 169 is-1 ta-153 sp-1 an-153 170 is-1 ta-154 sp-1 an-154 171 is-1 ta-155 sp-1 an-155 172 is-1 ta-156 sp-1 an-156 173 is-1 ta-157 sp-1 an-157 174 is-1 ta-158 sp-1 an-158 175 is-1 ta-159 sp-1 an-159 176 is-1 ta-160 sp-1 an-160 177 is-1 ta-161 sp-1 an-161 178 is-1 ta-162 sp-1 an-162 179 is-1 ta-163 sp-1 an-163 180 is-1 ta-164 sp-1 an-164 181 is-1 ta-165 sp-1 an-165 182 is-1 ta-166 sp-1 an-166 183 is-1 ta-167 sp-1 an-167 184 is-1 ta-168 sp-1 an-168 185 is-1 ta-169 sp-1 an-169 186 is-1 ta-170 sp-1 an-170 187 is-1 ta-171 sp-1 an-171 188 is-1 ta-172 sp-1 an-172 189 is-1 ta-173 sp-1 an-173 190 is-1 ta-174 sp-1 an-174 191 is-1 ta-175 sp-1 an-175 192 is-1 ta-176 sp-1 an-176 193 is-1 ta-177 sp-1 an-177 194 is-1 ta-178 sp-1 an-178 195 is-1 ta-179 sp-1 an-179 196 is-1 ta-180 sp-1 an-180 197 is-1 ta-181 sp-1 an-181 198 is-1 ta-182 sp-1 an-182 199 is-1 ta-183 sp-1 an-183 200 is-1 ta-184 sp-1 an-184 201 is-1 ta-185 sp-1 an-185 202 is-1 ta-186 sp-1 an-186 203 is-1 ta-187 sp-1 an-187 204 is-1 ta-188 sp-1 an-188 205 is-1 ta-189 sp-1 an-189 206 is-1 ta-190 sp-1 an-190 207 is-1 ta-191 sp-1 an-191 208 is-1 ta-192 sp-1 an-192 209 is-1 ta-193 sp-1 an-193 210 is-1 ta-194 sp-1 an-194 211 is-1 ta-195 sp-1 an-195 212 is-1 ta-196 sp-1 an-196 213 is-1 ta-197 sp-1 an-197 214 is-1 ta-198 sp-1 an-198 215 is-1 ta-199 sp-1 an-199 216 is-1 ta-200 sp-1 an-200 217 is-1 ta-201 sp-1 an-201 218 is-1 ta-202 sp-1 an-202 219 is-1 ta-203 sp-1 an-203 220 is-1 ta-204 sp-1 an-204 221 is-1 ta-205 sp-1 an-205 222 is-1 ta-206 sp-1 an-206 223 is-1 ta-207 sp-1 an-207 224 is-1 ta-208 sp-1 an-208 225 is-1 ta-209 sp-1 an-209 226 is-1 ta-210 sp-1 an-210 227 is-1 ta-211 sp-1 an-211 228 is-1 ta-212 sp-1 an-212 229 is-1 ta-213 sp-1 an-213 230 is-1 ta-214 sp-1 an-214 231 is-1 ta-215 sp-1 an-215 232 is-1 ta-216 sp-1 an-216 233 is-1 ta-217 sp-1 an-217 234 is-1 ta-218 sp-1 an-218 235 is-1 ta-219 sp-1 an-219 236 is-1 ta-220 sp-1 an-220 237 is-1 ta-221 sp-1 an-221 238 is-1 ta-222 sp-1 an-222 239 is-1 ta-223 sp-1 an-223 240 is-1 ta-224 sp-1 an-224 241 is-1 ta-225 sp-1 an-225 242 is-1 ta-226 sp-1 an-226 243 is-1 ta-227 sp-1 an-227 244 is-1 ta-228 sp-1 an-228 245 is-1 ta-229 sp-1 an-229 246 is-1 ta-230 sp-1 an-230 247 is-1 ta-231 sp-1 an-231 248 is-1 ta-232 sp-1 an-232 249 is-1 ta-233 sp-1 an-233 250 is-1 ta-234 sp-1 an-234 251 is-1 ta-235 sp-1 an-235 252 is-1 ta-236 sp-1 an-236 253 is-1 ta-237 sp-1 an-237 254 is-1 ta-238 sp-1 an-238 255 is-1 ta-239 sp-1 an-239 256 is-1 ta-240 sp-1 an-240 257 is-1 ta-241 sp-1 an-241 258 is-1 ta-242 sp-1 an-242 259 is-1 ta-243 sp-1 an-243 260 is-1 ta-244 sp-1 an-244 261 is-1 ta-245 sp-1 an-245 262 is-1 ta-246 sp-1 an-246 263 is-1 ta-247 sp-1 an-247 264 is-1 ta-248 sp-1 an-248 265 is-1 ta-249 sp-1 an-249 266 is-1 ta-250 sp-1 an-250 267 is-1 ta-251 sp-1 an-251 268 is-1 ta-252 sp-1 an-252 269 is-1 ta-253 sp-1 an-253 270 is-1 ta-254 sp-1 an-254 271 is-1 ta-255 sp-1 an-255 272 is-1 ta-256 sp-1 an-256 273 is-1 ta-257 sp-1 an-257 274 is-1 ta-258 sp-1 an-258 275 is-1 ta-259 sp-1 an-259 276 is-1 ta-260 sp-1 an-260 277 is-1 ta-261 sp-1 an-261 278 is-1 ta-262 sp-1 an-262 279 is-1 ta-263 sp-1 an-263 280 is-1 ta-264 sp-1 an-264 281 is-1 ta-265 sp-1 an-265 282 is-1 ta-266 sp-1 an-266 283 is-1 ta-267 sp-1 an-267 284 is-1 ta-268 sp-1 an-268 285 is-1 ta-269 sp-1 an-269 286 is-1 ta-270 sp-1 an-270 287 is-1 ta-271 sp-1 an-271 288 is-1 ta-272 sp-1 an-272 289 is-1 ta-273 sp-1 an-273 290 is-1 ta-274 sp-1 an-274 291 is-1 ta-275 sp-1 an-275 292 is-1 ta-276 sp-1 an-276 293 is-1 ta-277 sp-1 an-277 294 is-1 ta-278 sp-1 an-278 295 is-1 ta-279 sp-1 an-279 296 is-1 ta-280 sp-1 an-280 297 is-1 ta-281 sp-1 an-281 298 is-1 ta-282 sp-1 an-282 299 is-1 ta-283 sp-1 an-283 300 is-1 ta-284 sp-1 an-284 301 is-1 ta-285 sp-1 an-285 302 is-1 ta-286 sp-1 an-286 303 is-1 ta-287 sp-1 an-287 304 is-1 ta-288 sp-1 an-288 305 is-1 ta-289 sp-1 an-289 306 is-1 ta-290 sp-1 an-290 307 is-1 ta-291 sp-1 an-291 308 is-1 ta-292 sp-1 an-292 309 is-1 ta-293 sp-1 an-293 310 is-1 ta-294 sp-1 an-294 311 is-1 ta-295 sp-1 an-295 312 is-1 ta-296 sp-1 an-296 313 is-1 ta-297 sp-1 an-297 314 is-1 ta-298 sp-1 an-298 315 is-1 ta-299 sp-1 an-299 316 is-1 ta-300 sp-1 an-300 317 is-1 ta-301 sp-1 an-301 318 is-1 ta-302 sp-1 an-302 319 is-1 ta-303 sp-1 an-303 320 is-1 ta-304 sp-1 an-304 321 is-1 ta-305 sp-1 an-305 322 is-1 ta-306 sp-1 an-306 323 is-1 ta-307 sp-1 an-307 324 is-1 ta-308 sp-1 an-308 325 is-1 ta-309 sp-1 an-309 326 is-1 ta-310 sp-1 an-310 327 is-1 ta-311 sp-1 an-311 328 is-1 ta-312 sp-1 an-312 329 is-1 ta-313 sp-1 an-313 330 is-1 ta-314 sp-1 an-314 331 is-1 ta-315 sp-1 an-315 332 is-1 ta-316 sp-1 an-316 333 is-1 ta-317 sp-1 an-317 334 is-1 ta-318 sp-1 an-318 335 is-1 ta-319 sp-1 an-319 336 is-1 ta-320 sp-1 an-320 337 is-1 ta-321 sp-1 an-321 338 is-1 ta-322 sp-1 an-322 339 is-1 ta-323 sp-1 an-323 340 is-1 ta-324 sp-1 an-324 341 is-1 ta-325 sp-1 an-325 342 is-1 ta-326 sp-1 an-326 343 is-1 ta-327 sp-1 an-327 344 is-1 ta-328 sp-1 an-328 345 is-1 ta-329 sp-1 an-329 346 is-1 ta-330 sp-1 an-330 347 is-1 ta-331 sp-1 an-331 348 is-1 ta-332 sp-1 an-332 349 is-1 ta-333 sp-1 an-333 350 is-1 ta-334 sp-1 an-334 351 is-1 ta-335 sp-1 an-335 352 is-1 ta-336 sp-1 an-336 353 is-1 ta-337 sp-1 an-337 354 is-1 ta-338 sp-1 an-338 355 is-1 ta-339 sp-1 an-339 356 is-1 ta-340 sp-1 an-340 357 is-1 ta-341 sp-1 an-341 358 is-1 ta-342 sp-1 an-342 359 is-1 ta-343 sp-1 an-343 360 is-1 ta-344 sp-1 an-344 361 is-1 ta-345 sp-1 an-345 362 is-1 ta-346 sp-1 an-346 363 is-1 ta-347 sp-1 an-347 364 is-1 ta-348 sp-1 an-348 365 is-1 ta-349 sp-1 an-349 366 is-1 ta-350 sp-1 an-350 367 is-1 ta-351 sp-1 an-351 368 is-1 ta-352 sp-1 an-352 369 is-1 ta-353 sp-1 an-353 370 is-1 ta-354 sp-1 an-354 371 is-1 ta-355 sp-1 an-355 372 is-1 ta-356 sp-1 an-356 373 is-1 ta-357 sp-1 an-357 374 is-1 ta-358 sp-1 an-358 375 is-1 ta-359 sp-1 an-359 376 is-1 ta-360 sp-1 an-360 377 is-1 ta-361 sp-1 an-361 378 is-1 ta-362 sp-1 an-362 379 is-1 ta-363 sp-1 an-363 380 is-1 ta-364 sp-1 an-364 381 is-1 ta-365 sp-1 an-365 382 is-1 ta-366 sp-1 an-366 383 is-1 ta-367 sp-1 an-367 384 is-1 ta-368 sp-1 an-368 385 is-1 ta-369 sp-1 an-369 386 is-1 ta-370 sp-1 an-370 387 is-1 ta-371 sp-1 an-371 388 is-1 ta-372 sp-1 an-372 389 is-1 ta-373 sp-1 an-373 390 is-1 ta-374 sp-1 an-374 391 is-1 ta-375 sp-1 an-375 392 is-1 ta-376 sp-1 an-376 393 is-1 ta-377 sp-1 an-377 394 is-2 ta-1 sp-2 an-1 395 is-2 ta-2 sp-2 an-2 396 is-2 ta-3 sp-2 an-3 397 is-2 ta-4 sp-2 an-4 398 is-2 ta-5 sp-2 an-5 399 is-2 ta-6 sp-2 an-6 400 is-2 ta-7 sp-2 an-7 401 is-2 ta-8 sp-2 an-8 402 is-2 ta-9 sp-2 an-9 403 is-2 ta-10 sp-2 an-10 404 is-2 ta-11 sp-2 an-11 405 is-2 ta-12 sp-2 an-12 406 is-2 ta-13 sp-2 an-13 407 is-2 ta-14 sp-2 an-14 408 is-2 ta-15 sp-2 an-15 409 is-2 ta-16 sp-2 an-16 410 is-2 ta-17 sp-2 an-17 411 is-2 ta-18 sp-2 an-18 412 is-2 ta-19 sp-2 an-19 413 is-2 ta-20 sp-2 an-20 414 is-2 ta-21 sp-2 an-21 415 is-2 ta-22 sp-2 an-22 416 is-2 ta-23 sp-2 an-23 417 is-2 ta-24 sp-2 an-24 418 is-2 ta-25 sp-2 an-25 419 is-2 ta-26 sp-2 an-26 420 is-2 ta-27 sp-2 an-27 421 is-2 ta-28 sp-2 an-28 422 is-2 ta-29 sp-2 an-29 423 is-2 ta-30 sp-2 an-30 424 is-2 ta-31 sp-2 an-31 425 is-2 ta-32 sp-2 an-32 426 is-2 ta-33 sp-2 an-33 427 is-2 ta-34 sp-2 an-34 428 is-2 ta-35 sp-2 an-35 429 is-2 ta-36 sp-2 an-36 430 is-2 ta-37 sp-2 an-37 431 is-2 ta-38 sp-2 an-38 432 is-2 ta-39 sp-2 an-39 433 is-2 ta-40 sp-2 an-40 434 is-2 ta-41 sp-2 an-41 435 is-2 ta-42 sp-2 an-42 436 is-2 ta-43 sp-2 an-43 437 is-2 ta-44 sp-2 an-44 438 is-2 ta-45 sp-2 an-45 439 is-2 ta-46 sp-2 an-46 440 is-2 ta-47 sp-2 an-47 441 is-2 ta-48 sp-2 an-48 442 is-2 ta-49 sp-2 an-49 443 is-2 ta-50 sp-2 an-50 444 is-2 ta-51 sp-2 an-51 445 is-2 ta-52 sp-2 an-52 446 is-2 ta-53 sp-2 an-53 447 is-2 ta-54 sp-2 an-54 448 is-2 ta-55 sp-2 an-55 449 is-2 ta-56 sp-2 an-56 450 is-2 ta-57 sp-2 an-57 451 is-2 ta-58 sp-2 an-58 452 is-2 ta-59 sp-2 an-59 453 is-2 ta-60 sp-2 an-60 454 is-2 ta-61 sp-2 an-61 455 is-2 ta-62 sp-2 an-62 456 is-2 ta-63 sp-2 an-63 457 is-2 ta-64 sp-2 an-64 458 is-2 ta-65 sp-2 an-65 459 is-2 ta-66 sp-2 an-66 460 is-2 ta-67 sp-2 an-67 461 is-2 ta-68 sp-2 an-68 462 is-2 ta-69 sp-2 an-69 463 is-2 ta-70 sp-2 an-70 464 is-2 ta-71 sp-2 an-71 465 is-2 ta-72 sp-2 an-72 466 is-2 ta-73 sp-2 an-73 467 is-2 ta-74 sp-2 an-74 468 is-2 ta-75 sp-2 an-75 469 is-2 ta-76 sp-2 an-76 470 is-2 ta-77 sp-2 an-77 471 is-2 ta-78 sp-2 an-78 472 is-2 ta-79 sp-2 an-79 473 is-2 ta-80 sp-2 an-80 474 is-2 ta-81 sp-2 an-81 475 is-2 ta-82 sp-2 an-82 476 is-2 ta-83 sp-2 an-83 477 is-2 ta-84 sp-2 an-84 478 is-2 ta-85 sp-2 an-85 479 is-2 ta-86 sp-2 an-86 480 is-2 ta-87 sp-2 an-87 481 is-2 ta-88 sp-2 an-88 482 is-2 ta-89 sp-2 an-89 483 is-2 ta-90 sp-2 an-90 484 is-2 ta-91 sp-2 an-91 485 is-2 ta-92 sp-2 an-92 486 is-2 ta-93 sp-2 an-93 487 is-2 ta-94 sp-2 an-94 488 is-2 ta-95 sp-2 an-95 489 is-2 ta-96 sp-2 an-96 490 is-2 ta-97 sp-2 an-97 491 is-2 ta-98 sp-2 an-98 492 is-2 ta-99 sp-2 an-99 493 is-2 ta-100 sp-2 an-100 494 is-2 ta-101 sp-2 an-101 495 is-2 ta-102 sp-2 an-102 496 is-2 ta-103 sp-2 an-103 497 is-2 ta-104 sp-2 an-104 498 is-2 ta-105 sp-2 an-105 499 is-2 ta-106 sp-2 an-106 500 is-2 ta-107 sp-2 an-107 501 is-2 ta-108 sp-2 an-108 502 is-2 ta-109 sp-2 an-109 503 is-2 ta-110 sp-2 an-110 504 is-2 ta-111 sp-2 an-111 505 is-2 ta-112 sp-2 an-112 506 is-2 ta-113 sp-2 an-113 507 is-2 ta-114 sp-2 an-114 508 is-2 ta-115 sp-2 an-115 509 is-2 ta-116 sp-2 an-116 510 is-2 ta-117 sp-2 an-117 511 is-2 ta-118 sp-2 an-118 512 is-2 ta-119 sp-2 an-119 513 is-2 ta-120 sp-2 an-120 514 is-2 ta-121 sp-2 an-121 515 is-2 ta-122 sp-2 an-122 516 is-2 ta-123 sp-2 an-123 517 is-2 ta-124 sp-2 an-124 518 is-2 ta-125 sp-2 an-125 519 is-2 ta-126 sp-2 an-126 520 is-2 ta-127 sp-2 an-127 521 is-2 ta-128 sp-2 an-128 522 is-2 ta-129 sp-2 an-129 523 is-2 ta-130 sp-2 an-130 524 is-2 ta-131 sp-2 an-131 525 is-2 ta-132 sp-2 an-132 526 is-2 ta-133 sp-2 an-133 527 is-2 ta-134 sp-2 an-134 528 is-2 ta-135 sp-2 an-135 529 is-2 ta-136 sp-2 an-136 530 is-2 ta-137 sp-2 an-137 531 is-2 ta-138 sp-2 an-138 532 is-2 ta-139 sp-2 an-139 533 is-2 ta-140 sp-2 an-140 534 is-2 ta-141 sp-2 an-141 535 is-2 ta-142 sp-2 an-142 536 is-2 ta-143 sp-2 an-143 537 is-2 ta-144 sp-2 an-144 538 is-2 ta-145 sp-2 an-145 539 is-2 ta-146 sp-2 an-146 540 is-2 ta-147 sp-2 an-147 541 is-2 ta-148 sp-2 an-148 542 is-2 ta-149 sp-2 an-149 543 is-2 ta-150 sp-2 an-150 544 is-2 ta-151 sp-2 an-151 545 is-2 ta-152 sp-2 an-152 546 is-2 ta-153 sp-2 an-153 547 is-2 ta-154 sp-2 an-154 548 is-2 ta-155 sp-2 an-155 549 is-2 ta-156 sp-2 an-156 550 is-2 ta-157 sp-2 an-157 551 is-2 ta-158 sp-2 an-158 552 is-2 ta-159 sp-2 an-159 553 is-2 ta-160 sp-2 an-160 554 is-2 ta-161 sp-2 an-161 555 is-2 ta-162 sp-2 an-162 556 is-2 ta-163 sp-2 an-163 557 is-2 ta-164 sp-2 an-164 558 is-2 ta-165 sp-2 an-165 559 is-2 ta-166 sp-2 an-166 560 is-2 ta-167 sp-2 an-167 561 is-2 ta-168 sp-2 an-168 562 is-2 ta-169 sp-2 an-169 563 is-2 ta-170 sp-2 an-170 564 is-2 ta-171 sp-2 an-171 565 is-2 ta-172 sp-2 an-172 566 is-2 ta-173 sp-2 an-173 567 is-2 ta-174 sp-2 an-174 568 is-2 ta-175 sp-2 an-175 569 is-2 ta-176 sp-2 an-176 570 is-2 ta-177 sp-2 an-177 571 is-2 ta-178 sp-2 an-178 572 is-2 ta-179 sp-2 an-179 573 is-2 ta-180 sp-2 an-180 574 is-2 ta-181 sp-2 an-181 575 is-2 ta-182 sp-2 an-182 576 is-2 ta-183 sp-2 an-183 577 is-2 ta-184 sp-2 an-184 578 is-2 ta-185 sp-2 an-185 579 is-2 ta-186 sp-2 an-186 580 is-2 ta-187 sp-2 an-187 581 is-2 ta-188 sp-2 an-188 582 is-2 ta-189 sp-2 an-189 583 is-2 ta-190 sp-2 an-190 584 is-2 ta-191 sp-2 an-191 585 is-2 ta-192 sp-2 an-192 586 is-2 ta-193 sp-2 an-193 587 is-2 ta-194 sp-2 an-194 588 is-2 ta-195 sp-2 an-195 589 is-2 ta-196 sp-2 an-196 590 is-2 ta-197 sp-2 an-197 591 is-2 ta-198 sp-2 an-198 592 is-2 ta-199 sp-2 an-199 593 is-2 ta-200 sp-2 an-200 594 is-2 ta-201 sp-2 an-201 595 is-2 ta-202 sp-2 an-202 596 is-2 ta-203 sp-2 an-203 597 is-2 ta-204 sp-2 an-204 598 is-2 ta-205 sp-2 an-205 599 is-2 ta-206 sp-2 an-206 600 is-2 ta-207 sp-2 an-207 601 is-2 ta-208 sp-2 an-208 602 is-2 ta-209 sp-2 an-209 603 is-2 ta-210 sp-2 an-210 604 is-2 ta-211 sp-2 an-211 605 is-2 ta-212 sp-2 an-212 606 is-2 ta-213 sp-2 an-213 607 is-2 ta-214 sp-2 an-214 608 is-2 ta-215 sp-2 an-215 609 is-2 ta-216 sp-2 an-216 610 is-2 ta-217 sp-2 an-217 611 is-2 ta-218 sp-2 an-218 612 is-2 ta-219 sp-2 an-219 613 is-2 ta-220 sp-2 an-220 614 is-2 ta-221 sp-2 an-221 615 is-2 ta-222 sp-2 an-222 616 is-2 ta-223 sp-2 an-223 617 is-2 ta-224 sp-2 an-224 618 is-2 ta-225 sp-2 an-225 619 is-2 ta-226 sp-2 an-226 620 is-2 ta-227 sp-2 an-227 621 is-2 ta-228 sp-2 an-228 622 is-2 ta-229 sp-2 an-229 623 is-2 ta-230 sp-2 an-230 624 is-2 ta-231 sp-2 an-231 625 is-2 ta-232 sp-2 an-232 626 is-2 ta-233 sp-2 an-233 627 is-2 ta-234 sp-2 an-234 628 is-2 ta-235 sp-2 an-235 629 is-2 ta-236 sp-2 an-236 630 is-2 ta-237 sp-2 an-237 631 is-2 ta-238 sp-2 an-238 632 is-2 ta-239 sp-2 an-239 633 is-2 ta-240 sp-2 an-240 634 is-2 ta-241 sp-2 an-241 635 is-2 ta-242 sp-2 an-242 636 is-2 ta-243 sp-2 an-243 637 is-2 ta-244 sp-2 an-244 638 is-2 ta-245 sp-2 an-245 639 is-2 ta-246 sp-2 an-246 640 is-2 ta-247 sp-2 an-247 641 is-2 ta-248 sp-2 an-248 642 is-2 ta-249 sp-2 an-249 643 is-2 ta-250 sp-2 an-250 644 is-2 ta-251 sp-2 an-251 645 is-2 ta-252 sp-2 an-252 646 is-2 ta-253 sp-2 an-253 647 is-2 ta-254 sp-2 an-254 648 is-2 ta-255 sp-2 an-255 649 is-2 ta-256 sp-2 an-256 650 is-2 ta-257 sp-2 an-257 651 is-2 ta-258 sp-2 an-258 652 is-2 ta-259 sp-2 an-259 653 is-2 ta-260 sp-2 an-260 654 is-2 ta-261 sp-2 an-261 655 is-2 ta-262 sp-2 an-262 656 is-2 ta-263 sp-2 an-263 657 is-2 ta-264 sp-2 an-264 658 is-2 ta-265 sp-2 an-265 659 is-2 ta-266 sp-2 an-266 660 is-2 ta-267 sp-2 an-267 661 is-2 ta-268 sp-2 an-268 662 is-2 ta-269 sp-2 an-269 663 is-2 ta-270 sp-2 an-270 664 is-2 ta-271 sp-2 an-271 665 is-2 ta-272 sp-2 an-272 666 is-2 ta-273 sp-2 an-273 667 is-2 ta-274 sp-2 an-274 668 is-2 ta-275 sp-2 an-275 669 is-2 ta-276 sp-2 an-276 670 is-2 ta-277 sp-2 an-277 671 is-2 ta-278 sp-2 an-278 672 is-2 ta-279 sp-2 an-279 673 is-2 ta-280 sp-2 an-280 674 is-2 ta-281 sp-2 an-281 675 is-2 ta-282 sp-2 an-282 676 is-2 ta-283 sp-2 an-283 677 is-2 ta-284 sp-2 an-284 678 is-2 ta-285 sp-2 an-285 679 is-2 ta-286 sp-2 an-286 9 is-2 ta-287 sp-2 an-287 680 is-2 ta-288 sp-2 an-288 681 is-2 ta-289 sp-2 an-289 682 is-2 ta-290 sp-2 an-290 683 is-2 ta-291 sp-2 an-291 684 is-2 ta-292 sp-2 an-292 685 is-2 ta-293 sp-2 an-293 686 is-2 ta-294 sp-2 an-294 687 is-2 ta-295 sp-2 an-295 688 is-2 ta-296 sp-2 an-296 689 is-2 ta-297 sp-2 an-297 690 is-2 ta-298 sp-2 an-298 691 is-2 ta-299 sp-2 an-299 692 is-2 ta-300 sp-2 an-300 693 is-2 ta-301 sp-2 an-301 694 is-2 ta-302 sp-2 an-302 695 is-2 ta-303 sp-2 an-303 696 is-2 ta-304 sp-2 an-304 697 is-2 ta-305 sp-2 an-305 698 is-2 ta-306 sp-2 an-306 699 is-2 ta-307 sp-2 an-307 700 is-2 ta-308 sp-2 an-308 701 is-2 ta-309 sp-2 an-309 702 is-2 ta-310 sp-2 an-310 703 is-2 ta-311 sp-2 an-311 704 is-2 ta-312 sp-2 an-312 705 is-2 ta-313 sp-2 an-313 706 is-2 ta-314 sp-2 an-314 707 is-2 ta-315 sp-2 an-315 708 is-2 ta-316 sp-2 an-316 709 is-2 ta-317 sp-2 an-317 710 is-2 ta-318 sp-2 an-318 711 is-2 ta-319 sp-2 an-319 712 is-2 ta-320 sp-2 an-320 713 is-2 ta-321 sp-2 an-321 714 is-2 ta-322 sp-2 an-322 715 is-2 ta-323 sp-2 an-323 716 is-2 ta-324 sp-2 an-324 717 is-2 ta-325 sp-2 an-325 718 is-2 ta-326 sp-2 an-326 719 is-2 ta-327 sp-2 an-327 720 is-2 ta-328 sp-2 an-328 721 is-2 ta-329 sp-2 an-329 722 is-2 ta-330 sp-2 an-330 723 is-2 ta-331 sp-2 an-331 724 is-2 ta-332 sp-2 an-332 725 is-2 ta-333 sp-2 an-333 726 is-2 ta-334 sp-2 an-334 727 is-2 ta-335 sp-2 an-335 728 is-2 ta-336 sp-2 an-336 729 is-2 ta-337 sp-2 an-337 730 is-2 ta-338 sp-2 an-338 731 is-2 ta-339 sp-2 an-339 732 is-2 ta-340 sp-2 an-340 733 is-2 ta-341 sp-2 an-341 734 is-2 ta-342 sp-2 an-342 735 is-2 ta-343 sp-2 an-343 736 is-2 ta-344 sp-2 an-344 737 is-2 ta-345 sp-2 an-345 738 is-2 ta-346 sp-2 an-346 739 is-2 ta-347 sp-2 an-347 740 is-2 ta-348 sp-2 an-348 741 is-2 ta-349 sp-2 an-349 742 is-2 ta-350 sp-2 an-350 743 is-2 ta-351 sp-2 an-351 744 is-2 ta-352 sp-2 an-352 745 is-2 ta-353 sp-2 an-353 746 is-2 ta-354 sp-2 an-354 747 is-2 ta-355 sp-2 an-355 748 is-2 ta-356 sp-2 an-356 749 is-2 ta-357 sp-2 an-357 750 is-2 ta-358 sp-2 an-358 751 is-2 ta-359 sp-2 an-359 752 is-2 ta-360 sp-2 an-360 753 is-2 ta-361 sp-2 an-361 754 is-2 ta-362 sp-2 an-362 755 is-2 ta-363 sp-2 an-363 756 is-2 ta-364 sp-2 an-364 757 is-2 ta-365 sp-2 an-365 758 is-2 ta-366 sp-2 an-366 759 is-2 ta-367 sp-2 an-367 760 is-2 ta-368 sp-2 an-368 761 is-2 ta-369 sp-2 an-369 762 is-2 ta-370 sp-2 an-370 763 is-2 ta-371 sp-2 an-371 764 is-2 ta-372 sp-2 an-372 765 is-2 ta-373 sp-2 an-373 766 is-2 ta-374 sp-2 an-374 767 is-2 ta-375 sp-2 an-375 768 is-2 ta-376 sp-2 an-376 769 is-2 ta-377 sp-2 an-377 770 is-3 ta-1 sp-3 an-1 771 is-3 ta-2 sp-3 an-2 772 is-3 ta-3 sp-3 an-3 773 is-3 ta-4 sp-3 an-4 774 is-3 ta-5 sp-3 an-5 775 is-3 ta-6 sp-3 an-6 776 is-3 ta-7 sp-3 an-7 777 is-3 ta-8 sp-3 an-8 778 is-3 ta-9 sp-3 an-9 779 is-3 ta-10 sp-3 an-10 780 is-3 ta-11 sp-3 an-11 781 is-3 ta-12 sp-3 an-12 782 is-3 ta-13 sp-3 an-13 783 is-3 ta-14 sp-3 an-14 784 is-3 ta-15 sp-3 an-15 785 is-3 ta-16 sp-3 an-16 786 is-3 ta-17 sp-3 an-17 787 is-3 ta-18 sp-3 an-18 788 is-3 ta-19 sp-3 an-19 789 is-3 ta-20 sp-3 an-20 790 is-3 ta-21 sp-3 an-21 791 is-3 ta-22 sp-3 an-22 792 is-3 ta-23 sp-3 an-23 793 is-3 ta-24 sp-3 an-24 794 is-3 ta-25 sp-3 an-25 795 is-3 ta-26 sp-3 an-26 796 is-3 ta-27 sp-3 an-27 797 is-3 ta-28 sp-3 an-28 798 is-3 ta-29 sp-3 an-29 799 is-3 ta-30 sp-3 an-30 800 is-3 ta-31 sp-3 an-31 801 is-3 ta-32 sp-3 an-32 802 is-3 ta-33 sp-3 an-33 803 is-3 ta-34 sp-3 an-34 804 is-3 ta-35 sp-3 an-35 805 is-3 ta-36 sp-3 an-36 806 is-3 ta-37 sp-3 an-37 807 is-3 ta-38 sp-3 an-38 808 is-3 ta-39 sp-3 an-39 809 is-3 ta-40 sp-3 an-40 810 is-3 ta-41 sp-3 an-41 811 is-3 ta-42 sp-3 an-42 812 is-3 ta-43 sp-3 an-43 813 is-3 ta-44 sp-3 an-44 814 is-3 ta-45 sp-3 an-45 815 is-3 ta-46 sp-3 an-46 816 is-3 ta-47 sp-3 an-47 817 is-3 ta-48 sp-3 an-48 818 is-3 ta-49 sp-3 an-49 819 is-3 ta-50 sp-3 an-50 820 is-3 ta-51 sp-3 an-51 821 is-3 ta-52 sp-3 an-52 822 is-3 ta-53 sp-3 an-53 823 is-3 ta-54 sp-3 an-54 824 is-3 ta-55 sp-3 an-55 825 is-3 ta-56 sp-3 an-56 826 is-3 ta-57 sp-3 an-57 827 is-3 ta-58 sp-3 an-58 828 is-3 ta-59 sp-3 an-59 829 is-3 ta-60 sp-3 an-60 830 is-3 ta-61 sp-3 an-61 831 is-3 ta-62 sp-3 an-62 832 is-3 ta-63 sp-3 an-63 833 is-3 ta-64 sp-3 an-64 834 is-3 ta-65 sp-3 an-65 835 is-3 ta-66 sp-3 an-66 836 is-3 ta-67 sp-3 an-67 837 is-3 ta-68 sp-3 an-68 838 is-3 ta-69 sp-3 an-69 839 is-3 ta-70 sp-3 an-70 840 is-3 ta-71 sp-3 an-71 841 is-3 ta-72 sp-3 an-72 842 is-3 ta-73 sp-3 an-73 843 is-3 ta-74 sp-3 an-74 844 is-3 ta-75 sp-3 an-75 845 is-3 ta-76 sp-3 an-76 846 is-3 ta-77 sp-3 an-77 847 is-3 ta-78 sp-3 an-78 848 is-3 ta-79 sp-3 an-79 849 is-3 ta-80 sp-3 an-80 850 is-3 ta-81 sp-3 an-81 851 is-3 ta-82 sp-3 an-82 852 is-3 ta-83 sp-3 an-83 853 is-3 ta-84 sp-3 an-84 854 is-3 ta-85 sp-3 an-85 855 is-3 ta-86 sp-3 an-86 856 is-3 ta-87 sp-3 an-87 857 is-3 ta-88 sp-3 an-88 858 is-3 ta-89 sp-3 an-89 859 is-3 ta-90 sp-3 an-90 860 is-3 ta-91 sp-3 an-91 861 is-3 ta-92 sp-3 an-92 862 is-3 ta-93 sp-3 an-93 863 is-3 ta-94 sp-3 an-94 864 is-3 ta-95 sp-3 an-95 865 is-3 ta-96 sp-3 an-96 866 is-3 ta-97 sp-3 an-97 867 is-3 ta-98 sp-3 an-98 868 is-3 ta-99 sp-3 an-99 869 is-3 ta-100 sp-3 an-100 870 is-3 ta-101 sp-3 an-101 871 is-3 ta-102 sp-3 an-102 872 is-3 ta-103 sp-3 an-103 873 is-3 ta-104 sp-3 an-104 874 is-3 ta-105 sp-3 an-105 875 is-3 ta-106 sp-3 an-106 876 is-3 ta-107 sp-3 an-107 877 is-3 ta-108 sp-3 an-108 878 is-3 ta-109 sp-3 an-109 879 is-3 ta-110 sp-3 an-110 880 is-3 ta-111 sp-3 an-111 881 is-3 ta-112 sp-3 an-112 882 is-3 ta-113 sp-3 an-113 883 is-3 ta-114 sp-3 an-114 884 is-3 ta-115 sp-3 an-115 885 is-3 ta-116 sp-3 an-116 886 is-3 ta-117 sp-3 an-117 887 is-3 ta-118 sp-3 an-118 888 is-3 ta-119 sp-3 an-119 889 is-3 ta-120 sp-3 an-120 890 is-3 ta-121 sp-3 an-121 891 is-3 ta-122 sp-3 an-122 892 is-3 ta-123 sp-3 an-123 893 is-3 ta-124 sp-3 an-124 894 is-3 ta-125 sp-3 an-125 895 is-3 ta-126 sp-3 an-126 896 is-3 ta-127 sp-3 an-127 897 is-3 ta-128 sp-3 an-128 898 is-3 ta-129 sp-3 an-129 899 is-3 ta-130 sp-3 an-130 900 is-3 ta-131 sp-3 an-131 901 is-3 ta-132 sp-3 an-132 902 is-3 ta-133 sp-3 an-133 903 is-3 ta-134 sp-3 an-134 904 is-3 ta-135 sp-3 an-135 905 is-3 ta-136 sp-3 an-136 906 is-3 ta-137 sp-3 an-137 907 is-3 ta-138 sp-3 an-138 908 is-3 ta-139 sp-3 an-139 909 is-3 ta-140 sp-3 an-140 910 is-3 ta-141 sp-3 an-141 911 is-3 ta-142 sp-3 an-142 912 is-3 ta-143 sp-3 an-143 913 is-3 ta-144 sp-3 an-144 914 is-3 ta-145 sp-3 an-145 915 is-3 ta-146 sp-3 an-146 916 is-3 ta-147 sp-3 an-147 917 is-3 ta-148 sp-3 an-148 918 is-3 ta-149 sp-3 an-149 919 is-3 ta-150 sp-3 an-150 920 is-3 ta-151 sp-3 an-151 921 is-3 ta-152 sp-3 an-152 922 is-3 ta-153 sp-3 an-153 923 is-3 ta-154 sp-3 an-154 924 is-3 ta-155 sp-3 an-155 925 is-3 ta-156 sp-3 an-156 926 is-3 ta-157 sp-3 an-157 927 is-3 ta-158 sp-3 an-158 928 is-3 ta-159 sp-3 an-159 929 is-3 ta-160 sp-3 an-160 930 is-3 ta-161 sp-3 an-161 931 is-3 ta-162 sp-3 an-162 932 is-3 ta-163 sp-3 an-163 933 is-3 ta-164 sp-3 an-164 934 is-3 ta-165 sp-3 an-165 935 is-3 ta-166 sp-3 an-166 936 is-3 ta-167 sp-3 an-167 937 is-3 ta-168 sp-3 an-168 938 is-3 ta-169 sp-3 an-169 939 is-3 ta-170 sp-3 an-170 940 is-3 ta-171 sp-3 an-171 941 is-3 ta-172 sp-3 an-172 942 is-3 ta-173 sp-3 an-173 943 is-3 ta-174 sp-3 an-174 944 is-3 ta-175 sp-3 an-175 945 is-3 ta-176 sp-3 an-176 946 is-3 ta-177 sp-3 an-177 947 is-3 ta-178 sp-3 an-178 948 is-3 ta-179 sp-3 an-179 949 is-3 ta-180 sp-3 an-180 950 is-3 ta-181 sp-3 an-181 951 is-3 ta-182 sp-3 an-182 952 is-3 ta-183 sp-3 an-183 953 is-3 ta-184 sp-3 an-184 954 is-3 ta-185 sp-3 an-185 955 is-3 ta-186 sp-3 an-186 956 is-3 ta-187 sp-3 an-187 957 is-3 ta-188 sp-3 an-188 958 is-3 ta-189 sp-3 an-189 959 is-3 ta-190 sp-3 an-190 960 is-3 ta-191 sp-3 an-191 961 is-3 ta-192 sp-3 an-192 962 is-3 ta-193 sp-3 an-193 963 is-3 ta-194 sp-3 an-194 964 is-3 ta-195 sp-3 an-195 965 is-3 ta-196 sp-3 an-196 966 is-3 ta-197 sp-3 an-197 967 is-3 ta-198 sp-3 an-198 968 is-3 ta-199 sp-3 an-199 969 is-3 ta-200 sp-3 an-200 970 is-3 ta-201 sp-3 an-201 971 is-3 ta-202 sp-3 an-202 972 is-3 ta-203 sp-3 an-203 973 is-3 ta-204 sp-3 an-204 974 is-3 ta-205 sp-3 an-205 975 is-3 ta-206 sp-3 an-206 976 is-3 ta-207 sp-3 an-207 977 is-3 ta-208 sp-3 an-208 978 is-3 ta-209 sp-3 an-209 979 is-3 ta-210 sp-3 an-210 980 is-3 ta-211 sp-3 an-211 981 is-3 ta-212 sp-3 an-212 982 is-3 ta-213 sp-3 an-213 983 is-3 ta-214 sp-3 an-214 984 is-3 ta-215 sp-3 an-215 985 is-3 ta-216 sp-3 an-216 986 is-3 ta-217 sp-3 an-217 987 is-3 ta-218 sp-3 an-218 988 is-3 ta-219 sp-3 an-219 989 is-3 ta-220 sp-3 an-220 990 is-3 ta-221 sp-3 an-221 991 is-3 ta-222 sp-3 an-222 992 is-3 ta-223 sp-3 an-223 993 is-3 ta-224 sp-3 an-224 994 is-3 ta-225 sp-3 an-225 995 is-3 ta-226 sp-3 an-226 996 is-3 ta-227 sp-3 an-227 997 is-3 ta-228 sp-3 an-228 998 is-3 ta-229 sp-3 an-229 999 is-3 ta-230 sp-3 an-230 1000 is-3 ta-231 sp-3 an-231 1001 is-3 ta-232 sp-3 an-232 1002 is-3 ta-233 sp-3 an-233 1003 is-3 ta-234 sp-3 an-234 1004 is-3 ta-235 sp-3 an-235 1005 is-3 ta-236 sp-3 an-236 1006 is-3 ta-237 sp-3 an-237 1007 is-3 ta-238 sp-3 an-238 1008 is-3 ta-239 sp-3 an-239 1009 is-3 ta-240 sp-3 an-240 1010 is-3 ta-241 sp-3 an-241 1011 is-3 ta-242 sp-3 an-242 1012 is-3 ta-243 sp-3 an-243 1013 is-3 ta-244 sp-3 an-244 1014 is-3 ta-245 sp-3 an-245 1015 is-3 ta-246 sp-3 an-246 1016 is-3 ta-247 sp-3 an-247 1017 is-3 ta-248 sp-3 an-248 1018 is-3 ta-249 sp-3 an-249 1019 is-3 ta-250 sp-3 an-250 1020 is-3 ta-251 sp-3 an-251 1021 is-3 ta-252 sp-3 an-252 1022 is-3 ta-253 sp-3 an-253 1023 is-3 ta-254 sp-3 an-254 1024 is-3 ta-255 sp-3 an-255 1025 is-3 ta-256 sp-3 an-256 1026 is-3 ta-257 sp-3 an-257 1027 is-3 ta-258 sp-3 an-258 1028 is-3 ta-259 sp-3 an-259 1029 is-3 ta-260 sp-3 an-260 1030 is-3 ta-261 sp-3 an-261 1031 is-3 ta-262 sp-3 an-262 1032 is-3 ta-263 sp-3 an-263 1033 is-3 ta-264 sp-3 an-264 1034 is-3 ta-265 sp-3 an-265 1035 is-3 ta-266 sp-3 an-266 1036 is-3 ta-267 sp-3 an-267 1037 is-3 ta-268 sp-3 an-268 1038 is-3 ta-269 sp-3 an-269 1039 is-3 ta-270 sp-3 an-270 1040 is-3 ta-271 sp-3 an-271 1041 is-3 ta-272 sp-3 an-272 1042 is-3 ta-273 sp-3 an-273 1043 is-3 ta-274 sp-3 an-274 1044 is-3 ta-275 sp-3 an-275 1045 is-3 ta-276 sp-3 an-276 1046 is-3 ta-277 sp-3 an-277 1047 is-3 ta-278 sp-3 an-278 1048 is-3 ta-279 sp-3 an-279 1049 is-3 ta-280 sp-3 an-280 1050 is-3 ta-281 sp-3 an-281 1051 is-3 ta-282 sp-3 an-282 1052 is-3 ta-283 sp-3 an-283 1053 is-3 ta-284 sp-3 an-284 1054 is-3 ta-285 sp-3 an-285 1055 is-3 ta-286 sp-3 an-286 1056 is-3 ta-287 sp-3 an-287 1057 is-3 ta-288 sp-3 an-288 1058 is-3 ta-289 sp-3 an-289 1059 is-3 ta-290 sp-3 an-290 1060 is-3 ta-291 sp-3 an-291 1061 is-3 ta-292 sp-3 an-292 1062 is-3 ta-293 sp-3 an-293 1063 is-3 ta-294 sp-3 an-294 1064 is-3 ta-295 sp-3 an-295 1065 is-3 ta-296 sp-3 an-296 1066 is-3 ta-297 sp-3 an-297 1067 is-3 ta-298 sp-3 an-298 1068 is-3 ta-299 sp-3 an-299 1069 is-3 ta-300 sp-3 an-300 1070 is-3 ta-301 sp-3 an-301 1071 is-3 ta-302 sp-3 an-302 1072 is-3 ta-303 sp-3 an-303 1073 is-3 ta-304 sp-3 an-304 1074 is-3 ta-305 sp-3 an-305 1075 is-3 ta-306 sp-3 an-306 1076 is-3 ta-307 sp-3 an-307 1077 is-3 ta-308 sp-3 an-308 1078 is-3 ta-309 sp-3 an-309 1079 is-3 ta-310 sp-3 an-310 1080 is-3 ta-311 sp-3 an-311 1081 is-3 ta-312 sp-3 an-312 1082 is-3 ta-313 sp-3 an-313 1083 is-3 ta-314 sp-3 an-314 1084 is-3 ta-315 sp-3 an-315 1085 is-3 ta-316 sp-3 an-316 1086 is-3 ta-317 sp-3 an-317 1087 is-3 ta-318 sp-3 an-318 1088 is-3 ta-319 sp-3 an-319 1089 is-3 ta-320 sp-3 an-320 1090 is-3 ta-321 sp-3 an-321 1091 is-3 ta-322 sp-3 an-322 1092 is-3 ta-323 sp-3 an-323 1093 is-3 ta-324 sp-3 an-324 1094 is-3 ta-325 sp-3 an-325 1095 is-3 ta-326 sp-3 an-326 1096 is-3 ta-327 sp-3 an-327 1097 is-3 ta-328 sp-3 an-328 1098 is-3 ta-329 sp-3 an-329 1099 is-3 ta-330 sp-3 an-330 1100 is-3 ta-331 sp-3 an-331 1101 is-3 ta-332 sp-3 an-332 1102 is-3 ta-333 sp-3 an-333 1103 is-3 ta-334 sp-3 an-334 1104 is-3 ta-335 sp-3 an-335 1105 is-3 ta-336 sp-3 an-336 1106 is-3 ta-337 sp-3 an-337 1107 is-3 ta-338 sp-3 an-338 1108 is-3 ta-339 sp-3 an-339 1109 is-3 ta-340 sp-3 an-340 1110 is-3 ta-341 sp-3 an-341 1111 is-3 ta-342 sp-3 an-342 1112 is-3 ta-343 sp-3 an-343 1113 is-3 ta-344 sp-3 an-344 1114 is-3 ta-345 sp-3 an-345 1115 is-3 ta-346 sp-3 an-346 1116 is-3 ta-347 sp-3 an-347 1117 is-3 ta-348 sp-3 an-348 1118 is-3 ta-349 sp-3 an-349 1119 is-3 ta-350 sp-3 an-350 1120 is-3 ta-351 sp-3 an-351 1121 is-3 ta-352 sp-3 an-352 1122 is-3 ta-353 sp-3 an-353 1123 is-3 ta-354 sp-3 an-354 1124 is-3 ta-355 sp-3 an-355 1125 is-3 ta-356 sp-3 an-356 1126 is-3 ta-357 sp-3 an-357 1127 is-3 ta-358 sp-3 an-358 1128 is-3 ta-359 sp-3 an-359 1129 is-3 ta-360 sp-3 an-360 1130 is-3 ta-361 sp-3 an-361 1131 is-3 ta-362 sp-3 an-362 1132 is-3 ta-363 sp-3 an-363 1133 is-3 ta-364 sp-3 an-364 1134 is-3 ta-365 sp-3 an-365 1135 is-3 ta-366 sp-3 an-366 1136 is-3 ta-367 sp-3 an-367 1137 is-3 ta-368 sp-3 an-368 1138 is-3 ta-369 sp-3 an-369 1139 is-3 ta-370 sp-3 an-370 1140 is-3 ta-371 sp-3 an-371 1141 is-3 ta-372 sp-3 an-372 1142 is-3 ta-373 sp-3 an-373 1143 is-3 ta-374 sp-3 an-374 1144 is-3 ta-375 sp-3 an-375 1145 is-3 ta-376 sp-3 an-376 1146 is-3 ta-377 sp-3 an-377 1147 is-4 ta-1 sp-4 an-1 1148 is-4 ta-2 sp-4 an-2 1149 is-4 ta-3 sp-4 an-3 1150 is-4 ta-4 sp-4 an-4 1151 is-4 ta-5 sp-4 an-5 1152 is-4 ta-6 sp-4 an-6 1153 is-4 ta-7 sp-4 an-7 1154 is-4 ta-8 sp-4 an-8 1155 is-4 ta-9 sp-4 an-9 1156 is-4 ta-10 sp-4 an-10 1157 is-4 ta-11 sp-4 an-11 1158 is-4 ta-12 sp-4 an-12 1159 is-4 ta-13 sp-4 an-13 1160 is-4 ta-14 sp-4 an-14 1161 is-4 ta-15 sp-4 an-15 1162 is-4 ta-16 sp-4 an-16 1163 is-4 ta-17 sp-4 an-17 1164 is-4 ta-18 sp-4 an-18 1165 is-4 ta-19 sp-4 an-19 1166 is-4 ta-20 sp-4 an-20 1167 is-4 ta-21 sp-4 an-21 1168 is-4 ta-22 sp-4 an-22 1169 is-4 ta-23 sp-4 an-23 1170 is-4 ta-24 sp-4 an-24 1171 is-4 ta-25 sp-4 an-25 1172 is-4 ta-26 sp-4 an-26 1173 is-4 ta-27 sp-4 an-27 1174 is-4 ta-28 sp-4 an-28 1175 is-4 ta-29 sp-4 an-29 1176 is-4 ta-30 sp-4 an-30 1177 is-4 ta-31 sp-4 an-31 1178 is-4 ta-32 sp-4 an-32 1179 is-4 ta-33 sp-4 an-33 1180 is-4 ta-34 sp-4 an-34 1181 is-4 ta-35 sp-4 an-35 1182 is-4 ta-36 sp-4 an-36 1183 is-4 ta-37 sp-4 an-37 1184 is-4 ta-38 sp-4 an-38 1185 is-4 ta-39 sp-4 an-39 1186 is-4 ta-40 sp-4 an-40 1187 is-4 ta-41 sp-4 an-41 1188 is-4 ta-42 sp-4 an-42 1189 is-4 ta-43 sp-4 an-43 1190 is-4 ta-44 sp-4 an-44 1191 is-4 ta-45 sp-4 an-45 1192 is-4 ta-46 sp-4 an-46 1193 is-4 ta-47 sp-4 an-47 1194 is-4 ta-48 sp-4 an-48 1195 is-4 ta-49 sp-4 an-49 1196 is-4 ta-50 sp-4 an-50 1197 is-4 ta-51 sp-4 an-51 1198 is-4 ta-52 sp-4 an-52 1199 is-4 ta-53 sp-4 an-53 1200 is-4 ta-54 sp-4 an-54 1201 is-4 ta-55 sp-4 an-55 1202 is-4 ta-56 sp-4 an-56 1203 is-4 ta-57 sp-4 an-57 1204 is-4 ta-58 sp-4 an-58 1205 is-4 ta-59 sp-4 an-59 1206 is-4 ta-60 sp-4 an-60 1207 is-4 ta-61 sp-4 an-61 1208 is-4 ta-62 sp-4 an-62 1209 is-4 ta-63 sp-4 an-63 1210 is-4 ta-64 sp-4 an-64 1211 is-4 ta-65 sp-4 an-65 1212 is-4 ta-66 sp-4 an-66 1213 is-4 ta-67 sp-4 an-67 1214 is-4 ta-68 sp-4 an-68 1215 is-4 ta-69 sp-4 an-69 1216 is-4 ta-70 sp-4 an-70 1217 is-4 ta-71 sp-4 an-71 1218 is-4 ta-72 sp-4 an-72 1219 is-4 ta-73 sp-4 an-73 1220 is-4 ta-74 sp-4 an-74 1221 is-4 ta-75 sp-4 an-75 1222 is-4 ta-76 sp-4 an-76 1223 is-4 ta-77 sp-4 an-77 1224 is-4 ta-78 sp-4 an-78 1225 is-4 ta-79 sp-4 an-79 1226 is-4 ta-80 sp-4 an-80 1227 is-4 ta-81 sp-4 an-81 1228 is-4 ta-82 sp-4 an-82 1229 is-4 ta-83 sp-4 an-83 1230 is-4 ta-84 sp-4 an-84 1231 is-4 ta-85 sp-4 an-85 1232 is-4 ta-86 sp-4 an-86 1233 is-4 ta-87 sp-4 an-87 1234 is-4 ta-88 sp-4 an-88 1235 is-4 ta-89 sp-4 an-89 1236 is-4 ta-90 sp-4 an-90 1237 is-4 ta-91 sp-4 an-91 1238 is-4 ta-92 sp-4 an-92 1239 is-4 ta-93 sp-4 an-93 1240 is-4 ta-94 sp-4 an-94 1241 is-4 ta-95 sp-4 an-95 1242 is-4 ta-96 sp-4 an-96 1243 is-4 ta-97 sp-4 an-97 1244 is-4 ta-98 sp-4 an-98 1245 is-4 ta-99 sp-4 an-99 1246 is-4 ta-100 sp-4 an-100 1247 is-4 ta-101 sp-4 an-101 1248 is-4 ta-102 sp-4 an-102 1249 is-4 ta-103 sp-4 an-103 1250 is-4 ta-104 sp-4 an-104 1251 is-4 ta-105 sp-4 an-105 1252 is-4 ta-106 sp-4 an-106 1253 is-4 ta-107 sp-4 an-107 1254 is-4 ta-108 sp-4 an-108 1255 is-4 ta-109 sp-4 an-109 1256 is-4 ta-110 sp-4 an-110 1257 is-4 ta-111 sp-4 an-111 1258 is-4 ta-112 sp-4 an-112 1259 is-4 ta-113 sp-4 an-113 1260 is-4 ta-114 sp-4 an-114 1261 is-4 ta-115 sp-4 an-115 1262 is-4 ta-116 sp-4 an-116 1263 is-4 ta-117 sp-4 an-117 1264 is-4 ta-118 sp-4 an-118 1265 is-4 ta-119 sp-4 an-119 1266 is-4 ta-120 sp-4 an-120 1267 is-4 ta-121 sp-4 an-121 1268 is-4 ta-122 sp-4 an-122 1269 is-4 ta-123 sp-4 an-123 1270 is-4 ta-124 sp-4 an-124 1271 is-4 ta-125 sp-4 an-125 1272 is-4 ta-126 sp-4 an-126 1273 is-4 ta-127 sp-4 an-127 1274 is-4 ta-128 sp-4 an-128 1275 is-4 ta-129 sp-4 an-129 1276 is-4 ta-130 sp-4 an-130 1277 is-4 ta-131 sp-4 an-131 1278 is-4 ta-132 sp-4 an-132 1279 is-4 ta-133 sp-4 an-133 1280 is-4 ta-134 sp-4 an-134 1281 is-4 ta-135 sp-4 an-135 1282 is-4 ta-136 sp-4 an-136 1283 is-4 ta-137 sp-4 an-137 1284 is-4 ta-138 sp-4 an-138 1285 is-4 ta-139 sp-4 an-139 1286 is-4 ta-140 sp-4 an-140 1287 is-4 ta-141 sp-4 an-141 1288 is-4 ta-142 sp-4 an-142 1289 is-4 ta-143 sp-4 an-143 1290 is-4 ta-144 sp-4 an-144 1291 is-4 ta-145 sp-4 an-145 1292 is-4 ta-146 sp-4 an-146 1293 is-4 ta-147 sp-4 an-147 1294 is-4 ta-148 sp-4 an-148 1295 is-4 ta-149 sp-4 an-149 1296 is-4 ta-150 sp-4 an-150 1297 is-4 ta-151 sp-4 an-151 1298 is-4 ta-152 sp-4 an-152 1299 is-4 ta-153 sp-4 an-153 1300 is-4 ta-154 sp-4 an-154 1301 is-4 ta-155 sp-4 an-155 1302 is-4 ta-156 sp-4 an-156 1303 is-4 ta-157 sp-4 an-157 1304 is-4 ta-158 sp-4 an-158 1305 is-4 ta-159 sp-4 an-159 1306 is-4 ta-160 sp-4 an-160 1307 is-4 ta-161 sp-4 an-161 1308 is-4 ta-162 sp-4 an-162 1309 is-4 ta-163 sp-4 an-163 1310 is-4 ta-164 sp-4 an-164 1311 is-4 ta-165 sp-4 an-165 1312 is-4 ta-166 sp-4 an-166 1313 is-4 ta-167 sp-4 an-167 1314 is-4 ta-168 sp-4 an-168 1315 is-4 ta-169 sp-4 an-169 1316 is-4 ta-170 sp-4 an-170 1317 is-4 ta-171 sp-4 an-171 1318 is-4 ta-172 sp-4 an-172 1319 is-4 ta-173 sp-4 an-173 1320 is-4 ta-174 sp-4 an-174 1321 is-4 ta-175 sp-4 an-175 1322 is-4 ta-176 sp-4 an-176 1323 is-4 ta-177 sp-4 an-177 1324 is-4 ta-178 sp-4 an-178 1325 is-4 ta-179 sp-4 an-179 1326 is-4 ta-180 sp-4 an-180 1327 is-4 ta-181 sp-4 an-181 1328 is-4 ta-182 sp-4 an-182 1329 is-4 ta-183 sp-4 an-183 1330 is-4 ta-184 sp-4 an-184 1331 is-4 ta-185 sp-4 an-185 1332 is-4 ta-186 sp-4 an-186 1333 is-4 ta-187 sp-4 an-187 1334 is-4 ta-188 sp-4 an-188 1335 is-4 ta-189 sp-4 an-189 1336 is-4 ta-190 sp-4 an-190 1337 is-4 ta-191 sp-4 an-191 1338 is-4 ta-192 sp-4 an-192 1339 is-4 ta-193 sp-4 an-193 1340 is-4 ta-194 sp-4 an-194 1341 is-4 ta-195 sp-4 an-195 1342 is-4 ta-196 sp-4 an-196 1343 is-4 ta-197 sp-4 an-197 1344 is-4 ta-198 sp-4 an-198 1345 is-4 ta-199 sp-4 an-199 1346 is-4 ta-200 sp-4 an-200 1347 is-4 ta-201 sp-4 an-201 1348 is-4 ta-202 sp-4 an-202 1349 is-4 ta-203 sp-4 an-203 1350 is-4 ta-204 sp-4 an-204 1351 is-4 ta-205 sp-4 an-205 1352 is-4 ta-206 sp-4 an-206 1353 is-4 ta-207 sp-4 an-207 1354 is-4 ta-208 sp-4 an-208 1355 is-4 ta-209 sp-4 an-209 1356 is-4 ta-210 sp-4 an-210 1357 is-4 ta-211 sp-4 an-211 1358 is-4 ta-212 sp-4 an-212 1359 is-4 ta-213 sp-4 an-213 1360 is-4 ta-214 sp-4 an-214 1361 is-4 ta-215 sp-4 an-215 1362 is-4 ta-216 sp-4 an-216 1363 is-4 ta-217 sp-4 an-217 1364 is-4 ta-218 sp-4 an-218 1365 is-4 ta-219 sp-4 an-219 1366 is-4 ta-220 sp-4 an-220 1367 is-4 ta-221 sp-4 an-221 1368 is-4 ta-222 sp-4 an-222 1369 is-4 ta-223 sp-4 an-223 1370 is-4 ta-224 sp-4 an-224 1371 is-4 ta-225 sp-4 an-225 1372 is-4 ta-226 sp-4 an-226 1373 is-4 ta-227 sp-4 an-227 1374 is-4 ta-228 sp-4 an-228 1375 is-4 ta-229 sp-4 an-229 1376 is-4 ta-230 sp-4 an-230 1377 is-4 ta-231 sp-4 an-231 1378 is-4 ta-232 sp-4 an-232 1379 is-4 ta-233 sp-4 an-233 1380 is-4 ta-234 sp-4 an-234 1381 is-4 ta-235 sp-4 an-235 1382 is-4 ta-236 sp-4 an-236 1383 is-4 ta-237 sp-4 an-237 1384 is-4 ta-238 sp-4 an-238 1385 is-4 ta-239 sp-4 an-239 1386 is-4 ta-240 sp-4 an-240 1387 is-4 ta-241 sp-4 an-241 1388 is-4 ta-242 sp-4 an-242 1389 is-4 ta-243 sp-4 an-243 1390 is-4 ta-244 sp-4 an-244 1391 is-4 ta-245 sp-4 an-245 1392 is-4 ta-246 sp-4 an-246 1393 is-4 ta-247 sp-4 an-247 1394 is-4 ta-248 sp-4 an-248 1395 is-4 ta-249 sp-4 an-249 1396 is-4 ta-250 sp-4 an-250 1397 is-4 ta-251 sp-4 an-251 1398 is-4 ta-252 sp-4 an-252 1399 is-4 ta-253 sp-4 an-253 1400 is-4 ta-254 sp-4 an-254 1401 is-4 ta-255 sp-4 an-255 1402 is-4 ta-256 sp-4 an-256 1403 is-4 ta-257 sp-4 an-257 1404 is-4 ta-258 sp-4 an-258 1405 is-4 ta-259 sp-4 an-259 1406 is-4 ta-260 sp-4 an-260 1407 is-4 ta-261 sp-4 an-261 1408 is-4 ta-262 sp-4 an-262 1409 is-4 ta-263 sp-4 an-263 1410 is-4 ta-264 sp-4 an-264 1411 is-4 ta-265 sp-4 an-265 1412 is-4 ta-266 sp-4 an-266 1413 is-4 ta-267 sp-4 an-267 1414 is-4 ta-268 sp-4 an-268 1415 is-4 ta-269 sp-4 an-269 1416 is-4 ta-270 sp-4 an-270 1417 is-4 ta-271 sp-4 an-271 1418 is-4 ta-272 sp-4 an-272 1419 is-4 ta-273 sp-4 an-273 1420 is-4 ta-274 sp-4 an-274 1421 is-4 ta-275 sp-4 an-275 1422 is-4 ta-276 sp-4 an-276 1423 is-4 ta-277 sp-4 an-277 1424 is-4 ta-278 sp-4 an-278 1425 is-4 ta-279 sp-4 an-279 1426 is-4 ta-280 sp-4 an-280 1427 is-4 ta-281 sp-4 an-281 1428 is-4 ta-282 sp-4 an-282 1429 is-4 ta-283 sp-4 an-283 1430 is-4 ta-284 sp-4 an-284 1431 is-4 ta-285 sp-4 an-285 1432 is-4 ta-286 sp-4 an-286 1433 is-4 ta-287 sp-4 an-287 1434 is-4 ta-288 sp-4 an-288 1435 is-4 ta-289 sp-4 an-289 1436 is-4 ta-290 sp-4 an-290 1437 is-4 ta-291 sp-4 an-291 1438 is-4 ta-292 sp-4 an-292 1439 is-4 ta-293 sp-4 an-293 1440 is-4 ta-294 sp-4 an-294 1441 is-4 ta-295 sp-4 an-295 1442 is-4 ta-296 sp-4 an-296 1443 is-4 ta-297 sp-4 an-297 1444 is-4 ta-298 sp-4 an-298 1445 is-4 ta-299 sp-4 an-299 1446 is-4 ta-300 sp-4 an-300 1447 is-4 ta-301 sp-4 an-301 1448 is-4 ta-302 sp-4 an-302 1449 is-4 ta-303 sp-4 an-303 1450 is-4 ta-304 sp-4 an-304 1451 is-4 ta-305 sp-4 an-305 1452 is-4 ta-306 sp-4 an-306 1453 is-4 ta-307 sp-4 an-307 1454 is-4 ta-308 sp-4 an-308 1455 is-4 ta-309 sp-4 an-309 1456 is-4 ta-310 sp-4 an-310 1457 is-4 ta-311 sp-4 an-311 1458 is-4 ta-312 sp-4 an-312 1459 is-4 ta-313 sp-4 an-313 1460 is-4 ta-314 sp-4 an-314 1461 is-4 ta-315 sp-4 an-315 1462 is-4 ta-316 sp-4 an-316 1463 is-4 ta-317 sp-4 an-317 1464 is-4 ta-318 sp-4 an-318 1465 is-4 ta-319 sp-4 an-319 1466 is-4 ta-320 sp-4 an-320 1467 is-4 ta-321 sp-4 an-321 1468 is-4 ta-322 sp-4 an-322 1469 is-4 ta-323 sp-4 an-323 1470 is-4 ta-324 sp-4 an-324 1471 is-4 ta-325 sp-4 an-325 1472 is-4 ta-326 sp-4 an-326 1473 is-4 ta-327 sp-4 an-327 1474 is-4 ta-328 sp-4 an-328 1475 is-4 ta-329 sp-4 an-329 1476 is-4 ta-330 sp-4 an-330 1477 is-4 ta-331 sp-4 an-331 1478 is-4 ta-332 sp-4 an-332 1479 is-4 ta-333 sp-4 an-333 1480 is-4 ta-334 sp-4 an-334 1481 is-4 ta-335 sp-4 an-335 1482 is-4 ta-336 sp-4 an-336 1483 is-4 ta-337 sp-4 an-337 1484 is-4 ta-338 sp-4 an-338 1485 is-4 ta-339 sp-4 an-339 1486 is-4 ta-340 sp-4 an-340 1487 is-4 ta-341 sp-4 an-341 1488 is-4 ta-342 sp-4 an-342 1489 is-4 ta-343 sp-4 an-343 1490 is-4 ta-344 sp-4 an-344 1491 is-4 ta-345 sp-4 an-345 1492 is-4 ta-346 sp-4 an-346 1493 is-4 ta-347 sp-4 an-347 1494 is-4 ta-348 sp-4 an-348 1495 is-4 ta-349 sp-4 an-349 1496 is-4 ta-350 sp-4 an-350 1497 is-4 ta-351 sp-4 an-351 1498 is-4 ta-352 sp-4 an-352 1499 is-4 ta-353 sp-4 an-353 1500 is-4 ta-354 sp-4 an-354 1501 is-4 ta-355 sp-4 an-355 1502 is-4 ta-356 sp-4 an-356 1503 is-4 ta-357 sp-4 an-357 1504 is-4 ta-358 sp-4 an-358 1505 is-4 ta-359 sp-4 an-359 1506 is-4 ta-360 sp-4 an-360 1507 is-4 ta-361 sp-4 an-361 1508 is-4 ta-362 sp-4 an-362 1509 is-4 ta-363 sp-4 an-363 1510 is-4 ta-364 sp-4 an-364 1511 is-4 ta-365 sp-4 an-365 1512 is-4 ta-366 sp-4 an-366 1513 is-4 ta-367 sp-4 an-367 1514 is-4 ta-368 sp-4 an-368 1515 is-4 ta-369 sp-4 an-369 1516 is-4 ta-370 sp-4 an-370 1517 is-4 ta-371 sp-4 an-371 1518 is-4 ta-372 sp-4 an-372 1519 is-4 ta-373 sp-4 an-373 1520 is-4 ta-374 sp-4 an-374 1521 is-4 ta-375 sp-4 an-375 1522 is-4 ta-376 sp-4 an-376 1523 is-4 ta-377 sp-4 an-377 1524 is-5 ta-1 sp-5 an-1 1525 is-5 ta-2 sp-5 an-2 1526 is-5 ta-3 sp-5 an-3 1527 is-5 ta-4 sp-5 an-4 1528 is-5 ta-5 sp-5 an-5 1529 is-5 ta-6 sp-5 an-6 1530 is-5 ta-7 sp-5 an-7 1531 is-5 ta-8 sp-5 an-8 1532 is-5 ta-9 sp-5 an-9 1533 is-5 ta-10 sp-5 an-10 1534 is-5 ta-11 sp-5 an-11 1535 is-5 ta-12 sp-5 an-12 1536 is-5 ta-13 sp-5 an-13 1537 is-5 ta-14 sp-5 an-14 1538 is-5 ta-15 sp-5 an-15 1539 is-5 ta-16 sp-5 an-16 1540 is-5 ta-17 sp-5 an-17 1541 is-5 ta-18 sp-5 an-18 1542 is-5 ta-19 sp-5 an-19 1543 is-5 ta-20 sp-5 an-20 1544 is-5 ta-21 sp-5 an-21 1545 is-5 ta-22 sp-5 an-22 1546 is-5 ta-23 sp-5 an-23 1547 is-5 ta-24 sp-5 an-24 1548 is-5 ta-25 sp-5 an-25 1549 is-5 ta-26 sp-5 an-26 1550 is-5 ta-27 sp-5 an-27 1551 is-5 ta-28 sp-5 an-28 1552 is-5 ta-29 sp-5 an-29 1553 is-5 ta-30 sp-5 an-30 1554 is-5 ta-31 sp-5 an-31 1555 is-5 ta-32 sp-5 an-32 1556 is-5 ta-33 sp-5 an-33 1557 is-5 ta-34 sp-5 an-34 1558 is-5 ta-35 sp-5 an-35 1559 is-5 ta-36 sp-5 an-36 1560 is-5 ta-37 sp-5 an-37 1561 is-5 ta-38 sp-5 an-38 1562 is-5 ta-39 sp-5 an-39 1563 is-5 ta-40 sp-5 an-40 1564 is-5 ta-41 sp-5 an-41 1565 is-5 ta-42 sp-5 an-42 1566 is-5 ta-43 sp-5 an-43 1567 is-5 ta-44 sp-5 an-44 1568 is-5 ta-45 sp-5 an-45 1569 is-5 ta-46 sp-5 an-46 1570 is-5 ta-47 sp-5 an-47 1571 is-5 ta-48 sp-5 an-48 1572 is-5 ta-49 sp-5 an-49 1573 is-5 ta-50 sp-5 an-50 1574 is-5 ta-51 sp-5 an-51 1575 is-5 ta-52 sp-5 an-52 1576 is-5 ta-53 sp-5 an-53 1577 is-5 ta-54 sp-5 an-54 1578 is-5 ta-55 sp-5 an-55 1579 is-5 ta-56 sp-5 an-56 1580 is-5 ta-57 sp-5 an-57 1581 is-5 ta-58 sp-5 an-58 1582 is-5 ta-59 sp-5 an-59 1583 is-5 ta-60 sp-5 an-60 1584 is-5 ta-61 sp-5 an-61 1585 is-5 ta-62 sp-5 an-62 1586 is-5 ta-63 sp-5 an-63 1587 is-5 ta-64 sp-5 an-64 1588 is-5 ta-65 sp-5 an-65 1589 is-5 ta-66 sp-5 an-66 1590 is-5 ta-67 sp-5 an-67 1591 is-5 ta-68 sp-5 an-68 1592 is-5 ta-69 sp-5 an-69 1593 is-5 ta-70 sp-5 an-70 1594 is-5 ta-71 sp-5 an-71 1595 is-5 ta-72 sp-5 an-72 1596 is-5 ta-73 sp-5 an-73 1597 is-5 ta-74 sp-5 an-74 1598 is-5 ta-75 sp-5 an-75 1599 is-5 ta-76 sp-5 an-76 1600 is-5 ta-77 sp-5 an-77 1601 is-5 ta-78 sp-5 an-78 1602 is-5 ta-79 sp-5 an-79 1603 is-5 ta-80 sp-5 an-80 1604 is-5 ta-81 sp-5 an-81 1605 is-5 ta-82 sp-5 an-82 1606 is-5 ta-83 sp-5 an-83 1607 is-5 ta-84 sp-5 an-84 1608 is-5 ta-85 sp-5 an-85 1609 is-5 ta-86 sp-5 an-86 1610 is-5 ta-87 sp-5 an-87 1611 is-5 ta-88 sp-5 an-88 1612 is-5 ta-89 sp-5 an-89 1613 is-5 ta-90 sp-5 an-90 1614 is-5 ta-91 sp-5 an-91 1615 is-5 ta-92 sp-5 an-92 1616 is-5 ta-93 sp-5 an-93 1617 is-5 ta-94 sp-5 an-94 1618 is-5 ta-95 sp-5 an-95 1619 is-5 ta-96 sp-5 an-96 1620 is-5 ta-97 sp-5 an-97 1621 is-5 ta-98 sp-5 an-98 1622 is-5 ta-99 sp-5 an-99 1623 is-5 ta-100 sp-5 an-100 1624 is-5 ta-101 sp-5 an-101 1625 is-5 ta-102 sp-5 an-102 1626 is-5 ta-103 sp-5 an-103 1627 is-5 ta-104 sp-5 an-104 1628 is-5 ta-105 sp-5 an-105 1629 is-5 ta-106 sp-5 an-106 1630 is-5 ta-107 sp-5 an-107 1631 is-5 ta-108 sp-5 an-108 1632 is-5 ta-109 sp-5 an-109 1633 is-5 ta-110 sp-5 an-110 1634 is-5 ta-111 sp-5 an-111 1635 is-5 ta-112 sp-5 an-112 1636 is-5 ta-113 sp-5 an-113 1637 is-5 ta-114 sp-5 an-114 1638 is-5 ta-115 sp-5 an-115 1639 is-5 ta-116 sp-5 an-116 1640 is-5 ta-117 sp-5 an-117 1641 is-5 ta-118 sp-5 an-118 1642 is-5 ta-119 sp-5 an-119 1643 is-5 ta-120 sp-5 an-120 1644 is-5 ta-121 sp-5 an-121 1645 is-5 ta-122 sp-5 an-122 1646 is-5 ta-123 sp-5 an-123 1647 is-5 ta-124 sp-5 an-124 1648 is-5 ta-125 sp-5 an-125 1649 is-5 ta-126 sp-5 an-126 1650 is-5 ta-127 sp-5 an-127 1651 is-5 ta-128 sp-5 an-128 1652 is-5 ta-129 sp-5 an-129 1653 is-5 ta-130 sp-5 an-130 1654 is-5 ta-131 sp-5 an-131 1655 is-5 ta-132 sp-5 an-132 1656 is-5 ta-133 sp-5 an-133 1657 is-5 ta-134 sp-5 an-134 1658 is-5 ta-135 sp-5 an-135 1659 is-5 ta-136 sp-5 an-136 1660 is-5 ta-137 sp-5 an-137 1661 is-5 ta-138 sp-5 an-138 1662 is-5 ta-139 sp-5 an-139 1663 is-5 ta-140 sp-5 an-140 1664 is-5 ta-141 sp-5 an-141 1665 is-5 ta-142 sp-5 an-142 1666 is-5 ta-143 sp-5 an-143 1667 is-5 ta-144 sp-5 an-144 1668 is-5 ta-145 sp-5 an-145 1669 is-5 ta-146 sp-5 an-146 1670 is-5 ta-147 sp-5 an-147 1671 is-5 ta-148 sp-5 an-148 1672 is-5 ta-149 sp-5 an-149 1673 is-5 ta-150 sp-5 an-150 1674 is-5 ta-151 sp-5 an-151 1675 is-5 ta-152 sp-5 an-152 1676 is-5 ta-153 sp-5 an-153 1677 is-5 ta-154 sp-5 an-154 1678 is-5 ta-155 sp-5 an-155 1679 is-5 ta-156 sp-5 an-156 1680 is-5 ta-157 sp-5 an-157 1681 is-5 ta-158 sp-5 an-158 1682 is-5 ta-159 sp-5 an-159 1683 is-5 ta-160 sp-5 an-160 1684 is-5 ta-161 sp-5 an-161 1685 is-5 ta-162 sp-5 an-162 1686 is-5 ta-163 sp-5 an-163 1687 is-5 ta-164 sp-5 an-164 1688 is-5 ta-165 sp-5 an-165 1689 is-5 ta-166 sp-5 an-166 1690 is-5 ta-167 sp-5 an-167 1691 is-5 ta-168 sp-5 an-168 1692 is-5 ta-169 sp-5 an-169 1693 is-5 ta-170 sp-5 an-170 1694 is-5 ta-171 sp-5 an-171 1695 is-5 ta-172 sp-5 an-172 1696 is-5 ta-173 sp-5 an-173 1697 is-5 ta-174 sp-5 an-174 1698 is-5 ta-175 sp-5 an-175 1699 is-5 ta-176 sp-5 an-176 1700 is-5 ta-177 sp-5 an-177 1701 is-5 ta-178 sp-5 an-178 1702 is-5 ta-179 sp-5 an-179 1703 is-5 ta-180 sp-5 an-180 1704 is-5 ta-181 sp-5 an-181 1705 is-5 ta-182 sp-5 an-182 1706 is-5 ta-183 sp-5 an-183 1707 is-5 ta-184 sp-5 an-184 1708 is-5 ta-185 sp-5 an-185 1709 is-5 ta-186 sp-5 an-186 1710 is-5 ta-187 sp-5 an-187 1711 is-5 ta-188 sp-5 an-188 1712 is-5 ta-189 sp-5 an-189 1713 is-5 ta-190 sp-5 an-190 1714 is-5 ta-191 sp-5 an-191 1715 is-5 ta-192 sp-5 an-192 1716 is-5 ta-193 sp-5 an-193 1717 is-5 ta-194 sp-5 an-194 1718 is-5 ta-195 sp-5 an-195 1719 is-5 ta-196 sp-5 an-196 1720 is-5 ta-197 sp-5 an-197 1721 is-5 ta-198 sp-5 an-198 1722 is-5 ta-199 sp-5 an-199 1723 is-5 ta-200 sp-5 an-200 1724 is-5 ta-201 sp-5 an-201 1725 is-5 ta-202 sp-5 an-202 1726 is-5 ta-203 sp-5 an-203 1727 is-5 ta-204 sp-5 an-204 1728 is-5 ta-205 sp-5 an-205 1729 is-5 ta-206 sp-5 an-206 1730 is-5 ta-207 sp-5 an-207 1731 is-5 ta-208 sp-5 an-208 1732 is-5 ta-209 sp-5 an-209 1733 is-5 ta-210 sp-5 an-210 1734 is-5 ta-211 sp-5 an-211 1735 is-5 ta-212 sp-5 an-212 1736 is-5 ta-213 sp-5 an-213 1737 is-5 ta-214 sp-5 an-214 1738 is-5 ta-215 sp-5 an-215 1739 is-5 ta-216 sp-5 an-216 1740 is-5 ta-217 sp-5 an-217 1741 is-5 ta-218 sp-5 an-218 1742 is-5 ta-219 sp-5 an-219 1743 is-5 ta-220 sp-5 an-220 1744 is-5 ta-221 sp-5 an-221 1745 is-5 ta-222 sp-5 an-222 1746 is-5 ta-223 sp-5 an-223 1747 is-5 ta-224 sp-5 an-224 1748 is-5 ta-225 sp-5 an-225 1749 is-5 ta-226 sp-5 an-226 1750 is-5 ta-227 sp-5 an-227 1751 is-5 ta-228 sp-5 an-228 1752 is-5 ta-229 sp-5 an-229 1753 is-5 ta-230 sp-5 an-230 1754 is-5 ta-231 sp-5 an-231 1755 is-5 ta-232 sp-5 an-232 1756 is-5 ta-233 sp-5 an-233 1757 is-5 ta-234 sp-5 an-234 1758 is-5 ta-235 sp-5 an-235 1759 is-5 ta-236 sp-5 an-236 1760 is-5 ta-237 sp-5 an-237 1761 is-5 ta-238 sp-5 an-238 1762 is-5 ta-239 sp-5 an-239 1763 is-5 ta-240 sp-5 an-240 1764 is-5 ta-241 sp-5 an-241 1765 is-5 ta-242 sp-5 an-242 1766 is-5 ta-243 sp-5 an-243 1767 is-5 ta-244 sp-5 an-244 1768 is-5 ta-245 sp-5 an-245 1769 is-5 ta-246 sp-5 an-246 1770 is-5 ta-247 sp-5 an-247 1771 is-5 ta-248 sp-5 an-248 1772 is-5 ta-249 sp-5 an-249 1773 is-5 ta-250 sp-5 an-250 1774 is-5 ta-251 sp-5 an-251 1775 is-5 ta-252 sp-5 an-252 1776 is-5 ta-253 sp-5 an-253 1777 is-5 ta-254 sp-5 an-254 1778 is-5 ta-255 sp-5 an-255 1779 is-5 ta-256 sp-5 an-256 1780 is-5 ta-257 sp-5 an-257 1781 is-5 ta-258 sp-5 an-258 1782 is-5 ta-259 sp-5 an-259 1783 is-5 ta-260 sp-5 an-260 1784 is-5 ta-261 sp-5 an-261 1785 is-5 ta-262 sp-5 an-262 1786 is-5 ta-263 sp-5 an-263 1787 is-5 ta-264 sp-5 an-264 1788 is-5 ta-265 sp-5 an-265 1789 is-5 ta-266 sp-5 an-266 1790 is-5 ta-267 sp-5 an-267 1791 is-5 ta-268 sp-5 an-268 1792 is-5 ta-269 sp-5 an-269 1793 is-5 ta-270 sp-5 an-270 1794 is-5 ta-271 sp-5 an-271 1795 is-5 ta-272 sp-5 an-272 1796 is-5 ta-273 sp-5 an-273 1797 is-5 ta-274 sp-5 an-274 1798 is-5 ta-275 sp-5 an-275 1799 is-5 ta-276 sp-5 an-276 1800 is-5 ta-277 sp-5 an-277 1801 is-5 ta-278 sp-5 an-278 1802 is-5 ta-279 sp-5 an-279 1803 is-5 ta-280 sp-5 an-280 1804 is-5 ta-281 sp-5 an-281 1805 is-5 ta-282 sp-5 an-282 1806 is-5 ta-283 sp-5 an-283 1807 is-5 ta-284 sp-5 an-284 1808 is-5 ta-285 sp-5 an-285 1809 is-5 ta-286 sp-5 an-286 1810 is-5 ta-287 sp-5 an-287 1811 is-5 ta-288 sp-5 an-288 1812 is-5 ta-289 sp-5 an-289 1813 is-5 ta-290 sp-5 an-290 1814 is-5 ta-291 sp-5 an-291 1815 is-5 ta-292 sp-5 an-292 1816 is-5 ta-293 sp-5 an-293 1817 is-5 ta-294 sp-5 an-294 1818 is-5 ta-295 sp-5 an-295 1819 is-5 ta-296 sp-5 an-296 1820 is-5 ta-297 sp-5 an-297 1821 is-5 ta-298 sp-5 an-298 1822 is-5 ta-299 sp-5 an-299 1823 is-5 ta-300 sp-5 an-300 1824 is-5 ta-301 sp-5 an-301 1825 is-5 ta-302 sp-5 an-302 1826 is-5 ta-303 sp-5 an-303 1827 is-5 ta-304 sp-5 an-304 1828 is-5 ta-305 sp-5 an-305 1829 is-5 ta-306 sp-5 an-306 1830 is-5 ta-307 sp-5 an-307 1831 is-5 ta-308 sp-5 an-308 1832 is-5 ta-309 sp-5 an-309 1833 is-5 ta-310 sp-5 an-310 1834 is-5 ta-311 sp-5 an-311 1835 is-5 ta-312 sp-5 an-312 1836 is-5 ta-313 sp-5 an-313 1837 is-5 ta-314 sp-5 an-314 1838 is-5 ta-315 sp-5 an-315 1839 is-5 ta-316 sp-5 an-316 1840 is-5 ta-317 sp-5 an-317 1841 is-5 ta-318 sp-5 an-318 1842 is-5 ta-319 sp-5 an-319 1843 is-5 ta-320 sp-5 an-320 1844 is-5 ta-321 sp-5 an-321 1845 is-5 ta-322 sp-5 an-322 1846 is-5 ta-323 sp-5 an-323 1847 is-5 ta-324 sp-5 an-324 1848 is-5 ta-325 sp-5 an-325 1849 is-5 ta-326 sp-5 an-326 1850 is-5 ta-327 sp-5 an-327 1851 is-5 ta-328 sp-5 an-328 1852 is-5 ta-329 sp-5 an-329 1853 is-5 ta-330 sp-5 an-330 1854 is-5 ta-331 sp-5 an-331 1855 is-5 ta-332 sp-5 an-332 1856 is-5 ta-333 sp-5 an-333 1857 is-5 ta-334 sp-5 an-334 1858 is-5 ta-335 sp-5 an-335 1859 is-5 ta-336 sp-5 an-336 1860 is-5 ta-337 sp-5 an-337 1861 is-5 ta-338 sp-5 an-338 1862 is-5 ta-339 sp-5 an-339 1863 is-5 ta-340 sp-5 an-340 1864 is-5 ta-341 sp-5 an-341 1865 is-5 ta-342 sp-5 an-342 1866 is-5 ta-343 sp-5 an-343 1867 is-5 ta-344 sp-5 an-344 1868 is-5 ta-345 sp-5 an-345 1869 is-5 ta-346 sp-5 an-346 1870 is-5 ta-347 sp-5 an-347 1871 is-5 ta-348 sp-5 an-348 1872 is-5 ta-349 sp-5 an-349 1873 is-5 ta-350 sp-5 an-350 1874 is-5 ta-351 sp-5 an-351 1875 is-5 ta-352 sp-5 an-352 1876 is-5 ta-353 sp-5 an-353 1877 is-5 ta-354 sp-5 an-354 1878 is-5 ta-355 sp-5 an-355 1879 is-5 ta-356 sp-5 an-356 1880 is-5 ta-357 sp-5 an-357 1881 is-5 ta-358 sp-5 an-358 1882 is-5 ta-359 sp-5 an-359 1883 is-5 ta-360 sp-5 an-360 1884 is-5 ta-361 sp-5 an-361 1885 is-5 ta-362 sp-5 an-362 1886 is-5 ta-363 sp-5 an-363 1887 is-5 ta-364 sp-5 an-364 1888 is-5 ta-365 sp-5 an-365 1889 is-5 ta-366 sp-5 an-366 1890 is-5 ta-367 sp-5 an-367 1891 is-5 ta-368 sp-5 an-368 1892 is-5 ta-369 sp-5 an-369 1893 is-5 ta-370 sp-5 an-370 1894 is-5 ta-371 sp-5 an-371 1895 is-5 ta-372 sp-5 an-372 1896 is-5 ta-373 sp-5 an-373 1897 is-5 ta-374 sp-5 an-374 1898 is-5 ta-375 sp-5 an-375 1899 is-5 ta-376 sp-5 an-376 1900 is-5 ta-377 sp-5 an-377 1901 is-6 ta-1 sp-6 an-1 1902 is-6 ta-2 sp-6 an-2 1903 is-6 ta-3 sp-6 an-3 1904 is-6 ta-4 sp-6 an-4 1905 is-6 ta-5 sp-6 an-5 1906 is-6 ta-6 sp-6 an-6 1907 is-6 ta-7 sp-6 an-7 1908 is-6 ta-8 sp-6 an-8 1909 is-6 ta-9 sp-6 an-9 1910 is-6 ta-10 sp-6 an-10 1911 is-6 ta-11 sp-6 an-11 1912 is-6 ta-12 sp-6 an-12 1913 is-6 ta-13 sp-6 an-13 1914 is-6 ta-14 sp-6 an-14 1915 is-6 ta-15 sp-6 an-15 1916 is-6 ta-16 sp-6 an-16 1917 is-6 ta-17 sp-6 an-17 1918 is-6 ta-18 sp-6 an-18 1919 is-6 ta-19 sp-6 an-19 1920 is-6 ta-20 sp-6 an-20 1921 is-6 ta-21 sp-6 an-21 1922 is-6 ta-22 sp-6 an-22 1923 is-6 ta-23 sp-6 an-23 1924 is-6 ta-24 sp-6 an-24 1925 is-6 ta-25 sp-6 an-25 1926 is-6 ta-26 sp-6 an-26 1927 is-6 ta-27 sp-6 an-27 1928 is-6 ta-28 sp-6 an-28 1929 is-6 ta-29 sp-6 an-29 1930 is-6 ta-30 sp-6 an-30 1931 is-6 ta-31 sp-6 an-31 1932 is-6 ta-32 sp-6 an-32 1933 is-6 ta-33 sp-6 an-33 1934 is-6 ta-34 sp-6 an-34 1935 is-6 ta-35 sp-6 an-35 1936 is-6 ta-36 sp-6 an-36 1937 is-6 ta-37 sp-6 an-37 1938 is-6 ta-38 sp-6 an-38 1939 is-6 ta-39 sp-6 an-39 1940 is-6 ta-40 sp-6 an-40 1941 is-6 ta-41 sp-6 an-41 1942 is-6 ta-42 sp-6 an-42 1943 is-6 ta-43 sp-6 an-43 1944 is-6 ta-44 sp-6 an-44 1945 is-6 ta-45 sp-6 an-45 1946 is-6 ta-46 sp-6 an-46 1947 is-6 ta-47 sp-6 an-47 1948 is-6 ta-48 sp-6 an-48 1949 is-6 ta-49 sp-6 an-49 1950 is-6 ta-50 sp-6 an-50 1951 is-6 ta-51 sp-6 an-51 1952 is-6 ta-52 sp-6 an-52 1953 is-6 ta-53 sp-6 an-53 1954 is-6 ta-54 sp-6 an-54 1955 is-6 ta-55 sp-6 an-55 1956 is-6 ta-56 sp-6 an-56 1957 is-6 ta-57 sp-6 an-57 1958 is-6 ta-58 sp-6 an-58 1959 is-6 ta-59 sp-6 an-59 1960 is-6 ta-60 sp-6 an-60 1961 is-6 ta-61 sp-6 an-61 1962 is-6 ta-62 sp-6 an-62 1963 is-6 ta-63 sp-6 an-63 1964 is-6 ta-64 sp-6 an-64 1965 is-6 ta-65 sp-6 an-65 1966 is-6 ta-66 sp-6 an-66 1967 is-6 ta-67 sp-6 an-67 1968 is-6 ta-68 sp-6 an-68 1969 is-6 ta-69 sp-6 an-69 1970 is-6 ta-70 sp-6 an-70 1971 is-6 ta-71 sp-6 an-71 1972 is-6 ta-72 sp-6 an-72 1973 is-6 ta-73 sp-6 an-73 1974 is-6 ta-74 sp-6 an-74 1975 is-6 ta-75 sp-6 an-75 1976 is-6 ta-76 sp-6 an-76 1977 is-6 ta-77 sp-6 an-77 1978 is-6 ta-78 sp-6 an-78 1979 is-6 ta-79 sp-6 an-79 1980 is-6 ta-80 sp-6 an-80 1981 is-6 ta-81 sp-6 an-81 1982 is-6 ta-82 sp-6 an-82 1983 is-6 ta-83 sp-6 an-83 1984 is-6 ta-84 sp-6 an-84 1985 is-6 ta-85 sp-6 an-85 1986 is-6 ta-86 sp-6 an-86 1987 is-6 ta-87 sp-6 an-87 1988 is-6 ta-88 sp-6 an-88 1989 is-6 ta-89 sp-6 an-89 1990 is-6 ta-90 sp-6 an-90 1991 is-6 ta-91 sp-6 an-91 1992 is-6 ta-92 sp-6 an-92 1993 is-6 ta-93 sp-6 an-93 1994 is-6 ta-94 sp-6 an-94 1995 is-6 ta-95 sp-6 an-95 1996 is-6 ta-96 sp-6 an-96 1997 is-6 ta-97 sp-6 an-97 1998 is-6 ta-98 sp-6 an-98 1999 is-6 ta-99 sp-6 an-99 2000 is-6 ta-100 sp-6 an-100 2001 is-6 ta-101 sp-6 an-101 2002 is-6 ta-102 sp-6 an-102 2003 is-6 ta-103 sp-6 an-103 2004 is-6 ta-104 sp-6 an-104 2005 is-6 ta-105 sp-6 an-105 2006 is-6 ta-106 sp-6 an-106 2007 is-6 ta-107 sp-6 an-107 2008 is-6 ta-108 sp-6 an-108 2009 is-6 ta-109 sp-6 an-109 2010 is-6 ta-110 sp-6 an-110 2011 is-6 ta-111 sp-6 an-111 2012 is-6 ta-112 sp-6 an-112 2013 is-6 ta-113 sp-6 an-113 2014 is-6 ta-114 sp-6 an-114 2015 is-6 ta-115 sp-6 an-115 2016 is-6 ta-116 sp-6 an-116 2017 is-6 ta-117 sp-6 an-117 2018 is-6 ta-118 sp-6 an-118 2019 is-6 ta-119 sp-6 an-119 2020 is-6 ta-120 sp-6 an-120 2021 is-6 ta-121 sp-6 an-121 2022 is-6 ta-122 sp-6 an-122 2023 is-6 ta-123 sp-6 an-123 2024 is-6 ta-124 sp-6 an-124 2025 is-6 ta-125 sp-6 an-125 2026 is-6 ta-126 sp-6 an-126 2027 is-6 ta-127 sp-6 an-127 2028 is-6 ta-128 sp-6 an-128 2029 is-6 ta-129 sp-6 an-129 2030 is-6 ta-130 sp-6 an-130 2031 is-6 ta-131 sp-6 an-131 2032 is-6 ta-132 sp-6 an-132 2033 is-6 ta-133 sp-6 an-133 2034 is-6 ta-134 sp-6 an-134 2035 is-6 ta-135 sp-6 an-135 2036 is-6 ta-136 sp-6 an-136 2037 is-6 ta-137 sp-6 an-137 2038 is-6 ta-138 sp-6 an-138 2039 is-6 ta-139 sp-6 an-139 2040 is-6 ta-140 sp-6 an-140 2041 is-6 ta-141 sp-6 an-141 2042 is-6 ta-142 sp-6 an-142 2043 is-6 ta-143 sp-6 an-143 2044 is-6 ta-144 sp-6 an-144 2045 is-6 ta-145 sp-6 an-145 2046 is-6 ta-146 sp-6 an-146 2047 is-6 ta-147 sp-6 an-147 2048 is-6 ta-148 sp-6 an-148 2049 is-6 ta-149 sp-6 an-149 2050 is-6 ta-150 sp-6 an-150 2051 is-6 ta-151 sp-6 an-151 2052 is-6 ta-152 sp-6 an-152 2053 is-6 ta-153 sp-6 an-153 2054 is-6 ta-154 sp-6 an-154 2055 is-6 ta-155 sp-6 an-155 2056 is-6 ta-156 sp-6 an-156 2057 is-6 ta-157 sp-6 an-157 2058 is-6 ta-158 sp-6 an-158 2059 is-6 ta-159 sp-6 an-159 2060 is-6 ta-160 sp-6 an-160 2061 is-6 ta-161 sp-6 an-161 2062 is-6 ta-162 sp-6 an-162 2063 is-6 ta-163 sp-6 an-163 2064 is-6 ta-164 sp-6 an-164 2065 is-6 ta-165 sp-6 an-165 2066 is-6 ta-166 sp-6 an-166 2067 is-6 ta-167 sp-6 an-167 2068 is-6 ta-168 sp-6 an-168 2069 is-6 ta-169 sp-6 an-169 2070 is-6 ta-170 sp-6 an-170 2071 is-6 ta-171 sp-6 an-171 2072 is-6 ta-172 sp-6 an-172 2073 is-6 ta-173 sp-6 an-173 2074 is-6 ta-174 sp-6 an-174 2075 is-6 ta-175 sp-6 an-175 2076 is-6 ta-176 sp-6 an-176 2077 is-6 ta-177 sp-6 an-177 2078 is-8 ta-178 sp-6 an-178 2079 is-6 ta-179 sp-6 an-179 2080 is-6 ta-180 sp-6 an-180 2081 is-6 ta-181 sp-6 an-181 2082 is-6 ta-182 sp-6 an-182 2083 is-6 ta-183 sp-6 an-183 2084 is-6 ta-184 sp-6 an-184 2085 is-6 ta-185 sp-6 an-185 2086 is-6 ta-186 sp-6 an-186 2087 is-6 ta-187 sp-6 an-187 2088 is-6 ta-188 sp-6 an-188 2089 is-6 ta-189 sp-6 an-189 2090 is-6 ta-190 sp-6 an-190 2091 is-6 ta-191 sp-6 an-191 2092 is-6 ta-192 sp-6 an-192 2093 is-6 ta-193 sp-6 an-193 2094 is-6 ta-194 sp-6 an-194 2095 is-6 ta-195 sp-6 an-195 2096 is-6 ta-196 sp-6 an-196 2097 is-6 ta-197 sp-6 an-197 2098 is-6 ta-198 sp-6 an-198 2099 is-6 ta-199 sp-6 an-199 2100 is-6 ta-200 sp-6 an-200 2101 is-6 ta-201 sp-6 an-201 2102 is-6 ta-202 sp-6 an-202 2103 is-6 ta-203 sp-6 an-203 2104 is-6 ta-204 sp-6 an-204 2105 is-6 ta-205 sp-6 an-205 2106 is-6 ta-206 sp-6 an-206 2107 is-6 ta-207 sp-6 an-207 2108 is-6 ta-208 sp-6 an-208 2109 is-6 ta-209 sp-6 an-209 2110 is-6 ta-210 sp-6 an-210 2111 is-6 ta-211 sp-6 an-211 2112 is-6 ta-212 sp-6 an-212 2113 is-6 ta-213 sp-6 an-213 2114 is-6 ta-214 sp-6 an-214 2115 is-6 ta-215 sp-6 an-215 2116 is-6 ta-216 sp-6 an-216 2117 is-6 ta-217 sp-6 an-217 2118 is-6 ta-218 sp-6 an-218 2119 is-6 ta-219 sp-6 an-219 2120 is-6 ta-220 sp-6 an-220 2121 is-6 ta-221 sp-6 an-221 2122 is-6 ta-222 sp-6 an-222 2123 is-6 ta-223 sp-6 an-223 2124 is-6 ta-224 sp-6 an-224 2125 is-6 ta-225 sp-6 an-225 2126 is-6 ta-226 sp-6 an-226 2127 is-6 ta-227 sp-6 an-227 2128 is-6 ta-228 sp-6 an-228 2129 is-6 ta-229 sp-6 an-229 2130 is-6 ta-230 sp-6 an-230 2131 is-6 ta-231 sp-6 an-231 2132 is-6 ta-232 sp-6 an-232 2133 is-6 ta-233 sp-6 an-233 2134 is-6 ta-234 sp-6 an-234 2135 is-6 ta-235 sp-6 an-235 2136 is-6 ta-236 sp-6 an-236 2137 is-6 ta-237 sp-6 an-237 2138 is-6 ta-238 sp-6 an-238 2139 is-6 ta-239 sp-6 an-239 2140 is-6 ta-240 sp-6 an-240 2141 is-6 ta-241 sp-6 an-241 2142 is-6 ta-242 sp-6 an-242 2143 is-6 ta-243 sp-6 an-243 2144 is-6 ta-244 sp-6 an-244 2145 is-6 ta-245 sp-6 an-245 2146 is-6 ta-246 sp-6 an-246 2147 is-6 ta-247 sp-6 an-247 2148 is-6 ta-248 sp-6 an-248 2149 is-6 ta-249 sp-6 an-249 2150 is-6 ta-250 sp-6 an-250 2151 is-6 ta-251 sp-6 an-251 2152 is-6 ta-252 sp-6 an-252 2153 is-6 ta-253 sp-6 an-253 2154 is-6 ta-254 sp-6 an-254 2155 is-6 ta-255 sp-6 an-255 2156 is-6 ta-256 sp-6 an-256 2157 is-6 ta-257 sp-6 an-257 2158 is-6 ta-258 sp-6 an-258 2159 is-6 ta-259 sp-6 an-259 2160 is-6 ta-260 sp-6 an-260 2161 is-6 ta-261 sp-6 an-261 2162 is-6 ta-262 sp-6 an-262 2163 is-6 ta-263 sp-6 an-263 2164 is-6 ta-264 sp-6 an-264 2165 is-6 ta-265 sp-6 an-265 2166 is-6 ta-266 sp-6 an-266 2167 is-6 ta-267 sp-6 an-267 2168 is-6 ta-268 sp-6 an-268 2169 is-6 ta-269 sp-6 an-269 2170 is-6 ta-270 sp-6 an-270 2171 is-6 ta-271 sp-6 an-271 2172 is-6 ta-272 sp-6 an-272 2173 is-6 ta-273 sp-6 an-273 2174 is-6 ta-274 sp-6 an-274 2175 is-6 ta-275 sp-6 an-275 2176 is-6 ta-276 sp-6 an-276 2177 is-6 ta-277 sp-6 an-277 2178 is-6 ta-278 sp-6 an-278 2179 is-6 ta-279 sp-6 an-279 2180 is-6 ta-280 sp-6 an-280 2181 is-6 ta-281 sp-6 an-281 2182 is-6 ta-282 sp-6 an-282 2183 is-6 ta-283 sp-6 an-283 2184 is-6 ta-284 sp-6 an-284 2185 is-6 ta-285 sp-6 an-285 2186 is-6 ta-286 sp-6 an-286 2187 is-6 ta-287 sp-6 an-287 2188 is-6 ta-288 sp-6 an-288 2189 is-6 ta-289 sp-6 an-289 2190 is-6 ta-290 sp-6 an-290 2191 is-6 ta-291 sp-6 an-291 2192 is-6 ta-292 sp-6 an-292 2193 is-6 ta-293 sp-6 an-293 2194 is-6 ta-294 sp-6 an-294 2195 is-6 ta-295 sp-6 an-295 2196 is-6 ta-296 sp-6 an-296 2197 is-6 ta-297 sp-6 an-297 2198 is-6 ta-298 sp-6 an-298 2199 is-6 ta-299 sp-6 an-299 2200 is-6 ta-300 sp-6 an-300 2201 is-6 ta-301 sp-6 an-301 2202 is-6 ta-302 sp-6 an-302 2203 is-6 ta-303 sp-6 an-303 2204 is-6 ta-304 sp-6 an-304 2205 is-6 ta-305 sp-6 an-305 2206 is-6 ta-306 sp-6 an-306 2207 is-6 ta-307 sp-6 an-307 2208 is-6 ta-308 sp-6 an-308 2209 is-6 ta-309 sp-6 an-309 2210 is-6 ta-310 sp-6 an-310 2211 is-6 ta-311 sp-6 an-311 2212 is-6 ta-312 sp-6 an-312 2213 is-6 ta-313 sp-6 an-313 2214 is-6 ta-314 sp-6 an-314 2215 is-6 ta-315 sp-6 an-315 2216 is-6 ta-316 sp-6 an-316 2217 is-6 ta-317 sp-6 an-317 2218 is-6 ta-318 sp-6 an-318 2219 is-6 ta-319 sp-6 an-319 2220 is-6 ta-320 sp-6 an-320 2221 is-6 ta-321 sp-6 an-321 2222 is-6 ta-322 sp-6 an-322 2223 is-6 ta-323 sp-6 an-323 2224 is-6 ta-324 sp-6 an-324 2225 is-6 ta-325 sp-6 an-325 2226 is-6 ta-326 sp-6 an-326 2227 is-6 ta-327 sp-6 an-327 2228 is-6 ta-328 sp-6 an-328 2229 is-6 ta-329 sp-6 an-329 2230 is-6 ta-330 sp-6 an-330 2231 is-6 ta-331 sp-6 an-331 2232 is-6 ta-332 sp-6 an-332 2233 is-6 ta-333 sp-6 an-333 2234 is-6 ta-334 sp-6 an-334 2235 is-6 ta-335 sp-6 an-335 2236 is-6 ta-336 sp-6 an-336 2237 is-6 ta-337 sp-6 an-337 2238 is-6 ta-338 sp-6 an-338 2239 is-6 ta-339 sp-6 an-339 2240 is-6 ta-340 sp-6 an-340 2241 is-6 ta-341 sp-6 an-341 2242 is-6 ta-342 sp-6 an-342 2243 is-6 ta-343 sp-6 an-343 2244 is-6 ta-344 sp-6 an-344 2245 is-6 ta-345 sp-6 an-345 2246 is-6 ta-346 sp-6 an-346 2247 is-6 ta-347 sp-6 an-347 2248 is-6 ta-348 sp-6 an-348 2249 is-6 ta-349 sp-6 an-349 2250 is-6 ta-350 sp-6 an-350 2251 is-6 ta-351 sp-6 an-351 2252 is-6 ta-352 sp-6 an-352 2253 is-6 ta-353 sp-6 an-353 2254 is-6 ta-354 sp-6 an-354 2255 is-6 ta-355 sp-6 an-355 2256 is-6 ta-356 sp-6 an-356 2257 is-6 ta-357 sp-6 an-357 2258 is-6 ta-358 sp-6 an-358 2259 is-6 ta-359 sp-6 an-359 2260 is-6 ta-360 sp-6 an-360 2261 is-6 ta-361 sp-6 an-361 2262 is-6 ta-362 sp-6 an-362 2263 is-6 ta-363 sp-6 an-363 2264 is-6 ta-364 sp-6 an-364 2265 is-6 ta-365 sp-6 an-365 2266 is-6 ta-366 sp-6 an-366 2267 is-6 ta-367 sp-6 an-367 2268 is-6 ta-368 sp-6 an-368 2269 is-6 ta-369 sp-6 an-369 2270 is-6 ta-370 sp-6 an-370 2271 is-6 ta-371 sp-6 an-371 2272 is-6 ta-372 sp-6 an-372 2273 is-6 ta-373 sp-6 an-373 2274 is-6 ta-374 sp-6 an-374 2275 is-6 ta-375 sp-6 an-375 2276 is-6 ta-376 sp-6 an-376 2277 is-6 ta-377 sp-6 an-377 2278 is-7 ta-1 sp-7 an-1 2279 is-7 ta-2 sp-7 an-2 2280 is-7 ta-3 sp-7 an-3 2281 is-7 ta-4 sp-7 an-4 2282 is-7 ta-5 sp-7 an-5 2283 is-7 ta-6 sp-7 an-6 2284 is-7 ta-7 sp-7 an-7 2285 is-7 ta-8 sp-7 an-8 2286 is-7 ta-9 sp-7 an-9 2287 is-7 ta-10 sp-7 an-10 2288 is-7 ta-11 sp-7 an-11 2289 is-7 ta-12 sp-7 an-12 2290 is-7 ta-13 sp-7 an-13 2291 is-7 ta-14 sp-7 an-14 2292 is-7 ta-15 sp-7 an-15 2293 is-7 ta-16 sp-7 an-16 2294 is-7 ta-17 sp-7 an-17 2295 is-7 ta-18 sp-7 an-18 2296 is-7 ta-19 sp-7 an-19 2297 is-7 ta-20 sp-7 an-20 2298 is-7 ta-21 sp-7 an-21 2299 is-7 ta-22 sp-7 an-22 2300 is-7 ta-23 sp-7 an-23 2301 is-7 ta-24 sp-7 an-24 2302 is-7 ta-25 sp-7 an-25 2303 is-7 ta-26 sp-7 an-26 2304 is-7 ta-27 sp-7 an-27 2305 is-7 ta-28 sp-7 an-28 2306 is-7 ta-29 sp-7 an-29 2307 is-7 ta-30 sp-7 an-30 2308 is-7 ta-31 sp-7 an-31 2309 is-7 ta-32 sp-7 an-32 2310 is-7 ta-33 sp-7 an-33 2311 is-7 ta-34 sp-7 an-34 2312 is-7 ta-35 sp-7 an-35 2313 is-7 ta-36 sp-7 an-36 2314 is-7 ta-37 sp-7 an-37 2315 is-7 ta-38 sp-7 an-38 2316 is-7 ta-39 sp-7 an-39 2317 is-7 ta-40 sp-7 an-40 2318 is-7 ta-41 sp-7 an-41 2319 is-7 ta-42 sp-7 an-42 2320 is-7 ta-43 sp-7 an-43 2321 is-7 ta-44 sp-7 an-44 2322 is-7 ta-45 sp-7 an-45 2323 is-7 ta-46 sp-7 an-46 2324 is-7 ta-47 sp-7 an-47 2325 is-7 ta-48 sp-7 an-48 2326 is-7 ta-49 sp-7 an-49 2327 is-7 ta-50 sp-7 an-50 2328 is-7 ta-51 sp-7 an-51 2329 is-7 ta-52 sp-7 an-52 2330 is-7 ta-53 sp-7 an-53 2331 is-7 ta-54 sp-7 an-54 2332 is-7 ta-55 sp-7 an-55 2333 is-7 ta-56 sp-7 an-56 2334 is-7 ta-57 sp-7 an-57 2335 is-7 ta-58 sp-7 an-58 2336 is-7 ta-59 sp-7 an-59 2337 is-7 ta-60 sp-7 an-60 2338 is-7 ta-61 sp-7 an-61 2339 is-7 ta-62 sp-7 an-62 2340 is-7 ta-63 sp-7 an-63 2341 is-7 ta-64 sp-7 an-64 2342 is-7 ta-65 sp-7 an-65 2343 is-7 ta-66 sp-7 an-66 2344 is-7 ta-67 sp-7 an-67 2345 is-7 ta-68 sp-7 an-68 2346 is-7 ta-69 sp-7 an-69 2347 is-7 ta-70 sp-7 an-70 2348 is-7 ta-71 sp-7 an-71 2349 is-7 ta-72 sp-7 an-72 2350 is-7 ta-73 sp-7 an-73 2351 is-7 ta-74 sp-7 an-74 2352 is-7 ta-75 sp-7 an-75 2353 is-7 ta-76 sp-7 an-76 2354 is-7 ta-77 sp-7 an-77 2355 is-7 ta-78 sp-7 an-78 2356 is-7 ta-79 sp-7 an-79 2357 is-7 ta-80 sp-7 an-80 2358 is-7 ta-81 sp-7 an-81 2359 is-7 ta-82 sp-7 an-82 2360 is-7 ta-83 sp-7 an-83 2361 is-7 ta-84 sp-7 an-84 2362 is-7 ta-85 sp-7 an-85 2363 is-7 ta-86 sp-7 an-86 2364 is-7 ta-87 sp-7 an-87 2365 is-7 ta-88 sp-7 an-88 2366 is-7 ta-89 sp-7 an-89 2367 is-7 ta-90 sp-7 an-90 2368 is-7 ta-91 sp-7 an-91 2369 is-7 ta-92 sp-7 an-92 2370 is-7 ta-93 sp-7 an-93 2371 is-7 ta-94 sp-7 an-94 2372 is-7 ta-95 sp-7 an-95 2373 is-7 ta-96 sp-7 an-96 2374 is-7 ta-97 sp-7 an-97 2375 is-7 ta-98 sp-7 an-98 2376 is-7 ta-99 sp-7 an-99 2377 is-7 ta-100 sp-7 an-100 2378 is-7 ta-101 sp-7 an-101 2379 is-7 ta-102 sp-7 an-102 2380 is-7 ta-103 sp-7 an-103 2381 is-7 ta-104 sp-7 an-104 2382 is-7 ta-105 sp-7 an-105 2383 is-7 ta-106 sp-7 an-106 2384 is-7 ta-107 sp-7 an-107 2385 is-7 ta-108 sp-7 an-108 2386 is-7 ta-109 sp-7 an-109 2387 is-7 ta-110 sp-7 an-110 2388 is-7 ta-111 sp-7 an-111 2389 is-7 ta-112 sp-7 an-112 2390 is-7 ta-113 sp-7 an-113 2391 is-7 ta-114 sp-7 an-114 2392 is-7 ta-115 sp-7 an-115 2393 is-7 ta-116 sp-7 an-116 2394 is-7 ta-117 sp-7 an-117 2395 is-7 ta-118 sp-7 an-118 2396 is-7 ta-119 sp-7 an-119 2397 is-7 ta-120 sp-7 an-120 2398 is-7 ta-121 sp-7 an-121 2399 is-7 ta-122 sp-7 an-122 2400 is-7 ta-123 sp-7 an-123 2401 is-7 ta-124 sp-7 an-124 2402 is-7 ta-125 sp-7 an-125 2403 is-7 ta-126 sp-7 an-126 2404 is-7 ta-127 sp-7 an-127 2405 is-7 ta-128 sp-7 an-128 2406 is-7 ta-129 sp-7 an-129 2407 is-7 ta-130 sp-7 an-130 2408 is-7 ta-131 sp-7 an-131 2409 is-7 ta-132 sp-7 an-132 2410 is-7 ta-133 sp-7 an-133 2411 is-7 ta-134 sp-7 an-134 2412 is-7 ta-135 sp-7 an-135 2413 is-7 ta-136 sp-7 an-136 2414 is-7 ta-137 sp-7 an-137 2415 is-7 ta-138 sp-7 an-138 2416 is-7 ta-139 sp-7 an-139 2417 is-7 ta-140 sp-7 an-140 2418 is-7 ta-141 sp-7 an-141 2419 is-7 ta-142 sp-7 an-142 2420 is-7 ta-143 sp-7 an-143 2421 is-7 ta-144 sp-7 an-144 2422 is-7 ta-145 sp-7 an-145 2423 is-7 ta-146 sp-7 an-146 2424 is-7 ta-147 sp-7 an-147 2425 is-7 ta-148 sp-7 an-148 2426 is-7 ta-149 sp-7 an-149 2427 is-7 ta-150 sp-7 an-150 2428 is-7 ta-151 sp-7 an-151 2429 is-7 ta-152 sp-7 an-152 2430 is-7 ta-153 sp-7 an-153 2431 is-7 ta-154 sp-7 an-154 2432 is-7 ta-155 sp-7 an-155 2433 is-7 ta-156 sp-7 an-156 2434 is-7 ta-157 sp-7 an-157 2435 is-7 ta-158 sp-7 an-158 2436 is-7 ta-159 sp-7 an-159 2437 is-7 ta-160 sp-7 an-160 2438 is-7 ta-161 sp-7 an-161 2439 is-7 ta-162 sp-7 an-162 2440 is-7 ta-163 sp-7 an-163 2441 is-7 ta-164 sp-7 an-164 2442 is-7 ta-165 sp-7 an-165 2443 is-7 ta-166 sp-7 an-166 2444 is-7 ta-167 sp-7 an-167 2445 is-7 ta-168 sp-7 an-168 2446 is-7 ta-169 sp-7 an-169 2447 is-7 ta-170 sp-7 an-170 2448 is-7 ta-171 sp-7 an-171 2449 is-7 ta-172 sp-7 an-172 2450 is-7 ta-173 sp-7 an-173 2451 is-7 ta-174 sp-7 an-174 2452 is-7 ta-175 sp-7 an-175 2453 is-7 ta-176 sp-7 an-176 2454 is-7 ta-177 sp-7 an-177 2455 is-7 ta-178 sp-7 an-178 2456 is-7 ta-179 sp-7 an-179 2457 is-7 ta-180 sp-7 an-180 2458 is-7 ta-181 sp-7 an-181 2459 is-7 ta-182 sp-7 an-182 2460 is-7 ta-183 sp-7 an-183 2461 is-7 ta-184 sp-7 an-184 2462 is-7 ta-185 sp-7 an-185 2463 is-7 ta-186 sp-7 an-186 2464 is-7 ta-187 sp-7 an-187 2465 is-7 ta-188 sp-7 an-188 2466 is-7 ta-189 sp-7 an-189 2467 is-7 ta-190 sp-7 an-190 2468 is-7 ta-191 sp-7 an-191 2469 is-7 ta-192 sp-7 an-192 2470 is-7 ta-193 sp-7 an-193 2471 is-7 ta-194 sp-7 an-194 2472 is-7 ta-195 sp-7 an-195 2473 is-7 ta-196 sp-7 an-196 2474 is-7 ta-197 sp-7 an-197 2475 is-7 ta-198 sp-7 an-198 2476 is-7 ta-199 sp-7 an-199 2477 is-7 ta-200 sp-7 an-200 2478 is-7 ta-201 sp-7 an-201 2479 is-7 ta-202 sp-7 an-202 2480 is-7 ta-203 sp-7 an-203 2481 is-7 ta-204 sp-7 an-204 2482 is-7 ta-205 sp-7 an-205 2483 is-7 ta-206 sp-7 an-206 2484 is-7 ta-207 sp-7 an-207 2485 is-7 ta-208 sp-7 an-208 2486 is-7 ta-209 sp-7 an-209 2487 is-7 ta-210 sp-7 an-210 2488 is-7 ta-211 sp-7 an-211 2489 is-7 ta-212 sp-7 an-212 2490 is-7 ta-213 sp-7 an-213 2491 is-7 ta-214 sp-7 an-214 2492 is-7 ta-215 sp-7 an-215 2493 is-7 ta-216 sp-7 an-216 2494 is-7 ta-217 sp-7 an-217 2495 is-7 ta-218 sp-7 an-218 2496 is-7 ta-219 sp-7 an-219 2497 is-7 ta-220 sp-7 an-220 2498 is-7 ta-221 sp-7 an-221 2499 is-7 ta-222 sp-7 an-222 2500 is-7 ta-223 sp-7 an-223 2501 is-7 ta-224 sp-7 an-224 2502 is-7 ta-225 sp-7 an-225 2503 is-7 ta-226 sp-7 an-226 2504 is-7 ta-227 sp-7 an-227 2505 is-7 ta-228 sp-7 an-228 2506 is-7 ta-229 sp-7 an-229 2507 is-7 ta-230 sp-7 an-230 2508 is-7 ta-231 sp-7 an-231 2509 is-7 ta-232 sp-7 an-232 2510 is-7 ta-233 sp-7 an-233 2511 is-7 ta-234 sp-7 an-234 2512 is-7 ta-235 sp-7 an-235 2513 is-7 ta-236 sp-7 an-236 2514 is-7 ta-237 sp-7 an-237 2515 is-7 ta-238 sp-7 an-238 2516 is-7 ta-239 sp-7 an-239 2517 is-7 ta-240 sp-7 an-240 2518 is-7 ta-241 sp-7 an-241 2519 is-7 ta-242 sp-7 an-242 2520 is-7 ta-243 sp-7 an-243 2521 is-7 ta-244 sp-7 an-244 2522 is-7 ta-245 sp-7 an-245 2523 is-7 ta-246 sp-7 an-246 2524 is-7 ta-247 sp-7 an-247 2525 is-7 ta-248 sp-7 an-248 2526 is-7 ta-249 sp-7 an-249 2527 is-7 ta-250 sp-7 an-250 2528 is-7 ta-251 sp-7 an-251 2529 is-7 ta-252 sp-7 an-252 2530 is-7 ta-253 sp-7 an-253 2531 is-7 ta-254 sp-7 an-254 2532 is-7 ta-255 sp-7 an-255 2533 is-7 ta-256 sp-7 an-256 2534 is-7 ta-257 sp-7 an-257 2535 is-7 ta-258 sp-7 an-258 2536 is-7 ta-259 sp-7 an-259 2537 is-7 ta-260 sp-7 an-260 2538 is-7 ta-261 sp-7 an-261 2539 is-7 ta-262 sp-7 an-262 2540 is-7 ta-263 sp-7 an-263 2541 is-7 ta-264 sp-7 an-264 2542 is-7 ta-265 sp-7 an-265 2543 is-7 ta-266 sp-7 an-266 2544 is-7 ta-267 sp-7 an-267 2545 is-7 ta-268 sp-7 an-268 2546 is-7 ta-269 sp-7 an-269 2547 is-7 ta-270 sp-7 an-270 2548 is-7 ta-271 sp-7 an-271 2549 is-7 ta-272 sp-7 an-272 2550 is-7 ta-273 sp-7 an-273 2551 is-7 ta-274 sp-7 an-274 2552 is-7 ta-275 sp-7 an-275 2553 is-7 ta-276 sp-7 an-276 2554 is-7 ta-277 sp-7 an-277 2555 is-7 ta-278 sp-7 an-278 2556 is-7 ta-279 sp-7 an-279 2557 is-7 ta-280 sp-7 an-280 2558 is-7 ta-281 sp-7 an-281 2559 is-7 ta-282 sp-7 an-282 2560 is-7 ta-283 sp-7 an-283 2561 is-7 ta-284 sp-7 an-284 2562 is-7 ta-285 sp-7 an-285 2563 is-7 ta-286 sp-7 an-286 2564 is-7 ta-287 sp-7 an-287 2565 is-7 ta-288 sp-7 an-288 2566 is-7 ta-289 sp-7 an-289 2567 is-7 ta-290 sp-7 an-290 2568 is-7 ta-291 sp-7 an-291 2569 is-7 ta-292 sp-7 an-292 2570 is-7 ta-293 sp-7 an-293 2571 is-7 ta-294 sp-7 an-294 2572 is-7 ta-295 sp-7 an-295 2573 is-7 ta-296 sp-7 an-296 2574 is-7 ta-297 sp-7 an-297 2575 is-7 ta-298 sp-7 an-298 2576 is-7 ta-299 sp-7 an-299 2577 is-7 ta-300 sp-7 an-300 2578 is-7 ta-301 sp-7 an-301 2579 is-7 ta-302 sp-7 an-302 2580 is-7 ta-303 sp-7 an-303 2581 is-7 ta-304 sp-7 an-304 2582 is-7 ta-305 sp-7 an-305 2583 is-7 ta-306 sp-7 an-306 2584 is-7 ta-307 sp-7 an-307 2585 is-7 ta-308 sp-7 an-308 2586 is-7 ta-309 sp-7 an-309 2587 is-7 ta-310 sp-7 an-310 2588 is-7 ta-311 sp-7 an-311 2589 is-7 ta-312 sp-7 an-312 2590 is-7 ta-313 sp-7 an-313 2591 is-7 ta-314 sp-7 an-314 2592 is-7 ta-315 sp-7 an-315 2593 is-7 ta-316 sp-7 an-316 2594 is-7 ta-317 sp-7 an-317 2595 is-7 ta-318 sp-7 an-318 2596 is-7 ta-319 sp-7 an-319 2597 is-7 ta-320 sp-7 an-320 2598 is-7 ta-321 sp-7 an-321 2599 is-7 ta-322 sp-7 an-322 2600 is-7 ta-323 sp-7 an-323 2601 is-7 ta-324 sp-7 an-324 2602 is-7 ta-325 sp-7 an-325 2603 is-7 ta-326 sp-7 an-326 2604 is-7 ta-327 sp-7 an-327 2605 is-7 ta-328 sp-7 an-328 2606 is-7 ta-329 sp-7 an-329 2607 is-7 ta-330 sp-7 an-330 2608 is-7 ta-331 sp-7 an-331 2609 is-7 ta-332 sp-7 an-332 2610 is-7 ta-333 sp-7 an-333 2611 is-7 ta-334 sp-7 an-334 2612 is-7 ta-335 sp-7 an-335 2613 is-7 ta-336 sp-7 an-336 2614 is-7 ta-337 sp-7 an-337 2615 is-7 ta-338 sp-7 an-338 2616 is-7 ta-339 sp-7 an-339 2617 is-7 ta-340 sp-7 an-340 2618 is-7 ta-341 sp-7 an-341 2619 is-7 ta-342 sp-7 an-342 2620 is-7 ta-343 sp-7 an-343 2621 is-7 ta-344 sp-7 an-344 2622 is-7 ta-345 sp-7 an-345 2623 is-7 ta-346 sp-7 an-346 2624 is-7 ta-347 sp-7 an-347 2625 is-7 ta-348 sp-7 an-348 2626 is-7 ta-349 sp-7 an-349 2627 is-7 ta-350 sp-7 an-350 2628 is-7 ta-351 sp-7 an-351 2629 is-7 ta-352 sp-7 an-352 2630 is-7 ta-353 sp-7 an-353 2631 is-7 ta-354 sp-7 an-354 2632 is-7 ta-355 sp-7 an-355 2633 is-7 ta-356 sp-7 an-356 2634 is-7 ta-357 sp-7 an-357 2635 is-7 ta-358 sp-7 an-358 2636 is-7 ta-359 sp-7 an-359 2637 is-7 ta-360 sp-7 an-360 2638 is-7 ta-361 sp-7 an-361 2639 is-7 ta-362 sp-7 an-362 2640 is-7 ta-363 sp-7 an-363 2641 is-7 ta-364 sp-7 an-364 2642 is-7 ta-365 sp-7 an-365 2643 is-7 ta-366 sp-7 an-366 2644 is-7 ta-367 sp-7 an-367 2645 is-7 ta-368 sp-7 an-368 2646 is-7 ta-369 sp-7 an-369 2647 is-7 ta-370 sp-7 an-370 2648 is-7 ta-371 sp-7 an-371 2649 is-7 ta-372 sp-7 an-372 2650 is-7 ta-373 sp-7 an-373 2651 is-7 ta-374 sp-7 an-374 2652 is-7 ta-375 sp-7 an-375 2653 is-7 ta-376 sp-7 an-376 2654 is-7 ta-377 sp-7 an-377 2655 is-8 ta-1 sp-8 an-1 2656 is-8 ta-2 sp-8 an-2 2657 is-8 ta-3 sp-8 an-3 2658 is-8 ta-4 sp-8 an-4 2659 is-8 ta-5 sp-8 an-5 2660 is-8 ta-6 sp-8 an-6 2661 is-8 ta-7 sp-8 an-7 2662 is-8 ta-8 sp-8 an-8 2663 is-8 ta-9 sp-8 an-9 2664 is-8 ta-10 sp-8 an-10 2665 is-8 ta-11 sp-8 an-11 2666 is-8 ta-12 sp-8 an-12 2667 is-8 ta-13 sp-8 an-13 2668 is-8 ta-14 sp-8 an-14 2669 is-8 ta-15 sp-8 an-15 2670 is-8 ta-16 sp-8 an-16 2671 is-8 ta-17 sp-8 an-17 2672 is-8 ta-18 sp-8 an-18 2673 is-8 ta-19 sp-8 an-19 2674 is-8 ta-20 sp-8 an-20 2675 is-8 ta-21 sp-8 an-21 2676 is-8 ta-22 sp-8 an-22 2677 is-8 ta-23 sp-8 an-23 2678 is-8 ta-24 sp-8 an-24 2679 is-8 ta-25 sp-8 an-25 2680 is-8 ta-26 sp-8 an-26 2681 is-8 ta-27 sp-8 an-27 2682 is-8 ta-28 sp-8 an-28 2683 is-8 ta-29 sp-8 an-29 2684 is-8 ta-30 sp-8 an-30 2685 is-8 ta-31 sp-8 an-31 2686 is-8 ta-32 sp-8 an-32 2687 is-8 ta-33 sp-8 an-33 2688 is-8 ta-34 sp-8 an-34 2689 is-8 ta-35 sp-8 an-35 2690 is-8 ta-36 sp-8 an-36 2691 is-8 ta-37 sp-8 an-37 2692 is-8 ta-38 sp-8 an-38 2693 is-8 ta-39 sp-8 an-39 2694 is-8 ta-40 sp-8 an-40 2695 is-8 ta-41 sp-8 an-41 2696 is-8 ta-42 sp-8 an-42 2697 is-8 ta-43 sp-8 an-43 2698 is-8 ta-44 sp-8 an-44 2699 is-8 ta-45 sp-8 an-45 2700 is-8 ta-46 sp-8 an-46 2701 is-8 ta-47 sp-8 an-47 2702 is-8 ta-48 sp-8 an-48 2703 is-8 ta-49 sp-8 an-49 2704 is-8 ta-50 sp-8 an-50 2705 is-8 ta-51 sp-8 an-51 2706 is-8 ta-52 sp-8 an-52 2707 is-8 ta-53 sp-8 an-53 2708 is-8 ta-54 sp-8 an-54 2709 is-8 ta-55 sp-8 an-55 2710 is-8 ta-56 sp-8 an-56 2711 is-8 ta-57 sp-8 an-57 2712 is-8 ta-58 sp-8 an-58 2713 is-8 ta-59 sp-8 an-59 2714 is-8 ta-60 sp-8 an-60 2715 is-8 ta-61 sp-8 an-61 2716 is-8 ta-62 sp-8 an-62 2717 is-8 ta-63 sp-8 an-63 2718 is-8 ta-64 sp-8 an-64 2719 is-8 ta-65 sp-8 an-65 2720 is-8 ta-66 sp-8 an-66 2721 is-8 ta-67 sp-8 an-67 2722 is-8 ta-68 sp-8 an-68 2723 is-8 ta-69 sp-8 an-69 2724 is-8 ta-70 sp-8 an-70 2725 is-8 ta-71 sp-8 an-71 2726 is-8 ta-72 sp-8 an-72 2727 is-8 ta-73 sp-8 an-73 2728 is-8 ta-74 sp-8 an-74 2729 is-8 ta-75 sp-8 an-75 2730 is-8 ta-76 sp-8 an-76 2731 is-8 ta-77 sp-8 an-77 2732 is-8 ta-78 sp-8 an-78 2733 is-8 ta-79 sp-8 an-79 2734 is-8 ta-80 sp-8 an-80 2735 is-8 ta-81 sp-8 an-81 2736 is-8 ta-82 sp-8 an-82 2737 is-8 ta-83 sp-8 an-83 2738 is-8 ta-84 sp-8 an-84 2739 is-8 ta-85 sp-8 an-85 2740 is-8 ta-86 sp-8 an-86 2741 is-8 ta-87 sp-8 an-87 2742 is-8 ta-88 sp-8 an-88 2743 is-8 ta-89 sp-8 an-89 2744 is-8 ta-90 sp-8 an-90 2745 is-8 ta-91 sp-8 an-91 2746 is-8 ta-92 sp-8 an-92 2747 is-8 ta-93 sp-8 an-93 2748 is-8 ta-94 sp-8 an-94 2749 is-8 ta-95 sp-8 an-95 2750 is-8 ta-96 sp-8 an-96 2751 is-8 ta-97 sp-8 an-97 2752 is-8 ta-98 sp-8 an-98 2753 is-8 ta-99 sp-8 an-99 2754 is-8 ta-100 sp-8 an-100 2755 is-8 ta-101 sp-8 an-101 2756 is-8 ta-102 sp-8 an-102 2757 is-8 ta-103 sp-8 an-103 2758 is-8 ta-104 sp-8 an-104 2759 is-8 ta-105 sp-8 an-105 2760 is-8 ta-106 sp-8 an-106 2761 is-8 ta-107 sp-8 an-107 2762 is-8 ta-108 sp-8 an-108 2763 is-8 ta-109 sp-8 an-109 2764 is-8 ta-110 sp-8 an-110 2765 is-8 ta-111 sp-8 an-111 2766 is-8 ta-112 sp-8 an-112 2767 is-8 ta-113 sp-8 an-113 2768 is-8 ta-114 sp-8 an-114 2769 is-8 ta-115 sp-8 an-115 2770 is-8 ta-116 sp-8 an-116 2771 is-8 ta-117 sp-8 an-117 2772 is-8 ta-118 sp-8 an-118 2773 is-8 ta-119 sp-8 an-119 2774 is-8 ta-120 sp-8 an-120 2775 is-8 ta-121 sp-8 an-121 2776 is-8 ta-122 sp-8 an-122 2777 ia-8 ta-123 sp-8 an-123 2778 is-8 ta-124 sp-8 an-124 2779 is-8 ta-125 sp-8 an-125 2780 is-8 ta-126 sp-8 an-126 2781 is-8 ta-127 sp-8 an-127 2782 is-8 ta-128 sp-8 an-128 2783 is-8 ta-129 sp-8 an-129 2784 is-8 ta-130 sp-8 an-130 2785 is-8 ta-131 sp-8 an-131 2786 is-8 ta-132 sp-8 an-132 2787 is-8 ta-133 sp-8 an-133 2788 is-8 ta-134 sp-8 an-134 2789 is-8 ta-135 sp-8 an-135 2790 is-8 ta-136 sp-8 an-136 2791 is-8 ta-137 sp-8 an-137 2792 is-8 ta-138 sp-8 an-138 2793 is-8 ta-139 sp-8 an-139 2794 is-8 ta-140 sp-8 an-140 2795 is-8 ta-141 sp-8 an-141 2796 is-8 ta-142 sp-8 an-142 2797 is-8 ta-143 sp-8 an-143 2798 is-8 ta-144 sp-8 an-144 2799 is-8 ta-145 sp-8 an-145 2800 is-8 ta-146 sp-8 an-146 2801 is-8 ta-147 sp-8 an-147 2802 is-8 ta-148 sp-8 an-148 2803 is-8 ta-149 sp-8 an-149 2804 is-8 ta-150 sp-8 an-150 2805 is-8 ta-151 sp-8 an-151 2806 is-8 ta-152 sp-8 an-152 2807 is-8 ta-153 sp-8 an-153 2808 is-8 ta-154 sp-8 an-154 2809 is-8 ta-155 sp-8 an-155 2810 is-8 ta-156 sp-8 an-156 2811 is-8 ta-157 sp-8 an-157 2812 is-8 ta-158 sp-8 an-158 2813 is-8 ta-159 sp-8 an-159 2814 is-8 ta-160 sp-8 an-160 2815 is-8 ta-161 sp-8 an-161 2816 is-8 ta-162 sp-8 an-162 2817 is-8 ta-163 sp-8 an-163 2818 is-8 ta-164 sp-8 an-164 2819 is-8 ta-165 sp-8 an-165 2820 is-8 ta-166 sp-8 an-166 2821 is-8 ta-167 sp-8 an-167 2822 is-8 ta-168 sp-8 an-168 2823 is-8 ta-169 sp-8 an-169 2824 is-8 ta-170 sp-8 an-170 2825 is-8 ta-171 sp-8 an-171 2826 is-8 ta-172 sp-8 an-172 2827 is-8 ta-173 sp-8 an-173 2828 is-8 ta-174 sp-8 an-174 2829 is-8 ta-175 sp-8 an-175 2830 is-8 ta-176 sp-8 an-176 2831 is-8 ta-177 sp-8 an-177 2832 is-8 ta-178 sp-8 an-178 2833 is-8 ta-179 sp-8 an-179 2834 is-8 ta-180 sp-8 an-180 2835 is-8 ta-181 sp-8 an-181 2836 is-8 ta-182 sp-8 an-182 2837 is-8 ta-183 sp-8 an-183 2838 is-8 ta-184 sp-8 an-184 2839 is-8 ta-185 sp-8 an-185 2840 is-8 ta-186 sp-8 an-186 2841 is-8 ta-187 sp-8 an-187 2842 is-8 ta-188 sp-8 an-188 2843 is-8 ta-189 sp-8 an-189 2844 is-8 ta-190 sp-8 an-190 2845 is-8 ta-191 sp-8 an-191 2846 is-8 ta-192 sp-8 an-192 2847 is-8 ta-193 sp-8 an-193 2848 is-8 ta-194 sp-8 an-194 2849 is-8 ta-195 sp-8 an-195 2850 is-8 ta-196 sp-8 an-196 2851 is-8 ta-197 sp-8 an-197 2852 is-8 ta-198 sp-8 an-198 2853 is-8 ta-199 sp-8 an-199 2854 is-8 ta-200 sp-8 an-200 2855 is-8 ta-201 sp-8 an-201 2856 is-8 ta-202 sp-8 an-202 2857 is-8 ta-203 sp-8 an-203 2858 is-8 ta-204 sp-8 an-204 2859 is-8 ta-205 sp-8 an-205 2860 is-8 ta-206 sp-8 an-206 2861 is-8 ta-207 sp-8 an-207 2862 is-8 ta-208 sp-8 an-208 2863 is-8 ta-209 sp-8 an-209 2864 is-8 ta-210 sp-8 an-210 2865 is-8 ta-211 sp-8 an-211 2866 is-8 ta-212 sp-8 an-212 2867 is-8 ta-213 sp-8 an-213 2868 is-8 ta-214 sp-8 an-214 2869 is-8 ta-215 sp-8 an-215 2870 is-8 ta-216 sp-8 an-216 2871 is-8 ta-217 sp-8 an-217 2872 is-8 ta-218 sp-8 an-218 2873 is-8 ta-219 sp-8 an-219 2874 is-8 ta-220 sp-8 an-220 2875 is-8 ta-221 sp-8 an-221 2876 is-8 ta-222 sp-8 an-222 2877 is-8 ta-223 sp-8 an-223 2878 is-8 ta-224 sp-8 an-224 2879 is-8 ta-225 sp-8 an-225 2880 is-8 ta-226 sp-8 an-226 2881 is-8 ta-227 sp-8 an-227 2882 is-8 ta-228 sp-8 an-228 2833 is-8 ta-229 sp-8 an-229 2884 is-8 ta-230 sp-8 an-230 2885 is-8 ta-231 sp-8 an-231 2886 is-8 ta-232 sp-8 an-232 2887 is-8 ta-233 sp-8 an-233 2888 is-8 ta-234 sp-8 an-234 2889 is-8 ta-235 sp-8 an-235 2890 is-8 ta-236 sp-8 an-236 2891 is-8 ta-237 sp-8 an-237 2892 is-8 ta-238 sp-8 an-238 2893 is-8 ta-239 sp-8 an-239 2894 is-8 ta-240 sp-8 an-240 2895 is-8 ta-241 sp-8 an-241 2896 is-8 ta-242 sp-8 an-242 2897 is-8 ta-243 sp-8 an-243 2898 is-8 ta-244 sp-8 an-244 2899 is-8 ta-245 sp-8 an-245 2900 is-8 ta-246 sp-8 an-246 2901 is-8 ta-247 sp-8 an-247 2902 is-8 ta-248 sp-8 an-248 2903 is-8 ta-249 sp-8 an-249 2904 is-8 ta-250 sp-8 an-250 2905 is-8 ta-251 sp-8 an-251 2906 is-8 ta-252 sp-8 an-252 2907 is-8 ta-253 sp-8 an-253 2908 is-8 ta-254 sp-8 an-254 2909 is-8 ta-255 sp-8 an-255 2910 is-8 ta-256 sp-8 an-256 2911 is-8 ta-257 sp-8 an-257 2912 is-8 ta-258 sp-8 an-258 2913 is-8 ta-259 sp-8 an-259 2914 is-8 ta-260 sp-8 an-260 2915 is-8 ta-261 sp-8 an-261 2916 is-8 ta-262 sp-8 an-262 2917 is-8 ta-263 sp-8 an-263 2918 is-8 ta-264 sp-8 an-264 2919 is-8 ta-265 sp-8 an-265 2920 is-8 ta-266 sp-8 an-266 2921 is-8 ta-267 sp-8 an-267 2922 is-8 ta-268 sp-8 an-268 2923 is-8 ta-269 sp-8 an-269 2924 is-8 ta-270 sp-8 an-270 2925 is-8 ta-271 sp-8 an-271 2926 is-8 ta-272 sp-8 an-272 2927 is-8 ta-273 sp-8 an-273 2928 is-8 ta-274 sp-8 an-274 2929 is-8 ta-275 sp-8 an-275 2930 is-8 ta-276 sp-8 an-276 2931 is-8 ta-277 sp-8 an-277 2932 is-8 ta-278 sp-8 an-278 2933 is-8 ta-279 sp-8 an-279 2934 is-8 ta-280 sp-8 an-280 2935 is-8 ta-281 sp-8 an-281 2936 is-8 ta-282 sp-8 an-282 2937 is-8 ta-283 sp-8 an-283 2938 is-8 ta-284 sp-8 an-284 2939 is-8 ta-285 sp-8 an-285 2940 is-8 ta-286 sp-8 an-286 2941 is-8 ta-287 sp-8 an-287 2942 is-8 ta-288 sp-8 an-288 2943 is-8 ta-289 sp-8 an-289 2944 is-8 ta-290 sp-8 an-290 2945 is-8 ta-291 sp-8 an-291 2946 is-8 ta-292 sp-8 an-292 2947 is-8 ta-293 sp-8 an-293 2948 is-8 ta-294 sp-8 an-294 2949 is-8 ta-295 sp-8 an-295 2950 is-8 ta-296 sp-8 an-296 2951 is-8 ta-297 sp-8 an-297 2952 is-8 ta-298 sp-8 an-298 2953 is-8 ta-299 sp-8 an-299 2954 is-8 ta-300 sp-8 an-300 2955 is-8 ta-301 sp-8 an-301 2956 is-8 ta-302 sp-8 an-302 2957 is-8 ta-303 sp-8 an-303 2958 is-8 ta-304 sp-8 an-304 2959 is-8 ta-305 sp-8 an-305 2960 is-8 ta-306 sp-8 an-306 2961 is-8 ta-307 sp-8 an-307 2962 is-8 ta-308 sp-8 an-308 2963 is-8 ta-309 sp-8 an-309 2964 is-8 ta-310 sp-8 an-310 2965 is-8 ta-311 sp-8 an-311 2966 is-8 ta-312 sp-8 an-312 2967 is-8 ta-313 sp-8 an-313 2968 is-8 ta-314 sp-8 an-314 2969 is-8 ta-315 sp-8 an-315 2970 is-8 ta-316 sp-8 an-316 2971 is-8 ta-317 sp-8 an-317 2972 is-8 ta-318 sp-8 an-318 2973 is-8 ta-319 sp-8 an-319 2974 is-8 ta-320 sp-8 an-320 2975 is-8 ta-321 sp-8 an-321 2976 is-8 ta-322 sp-8 an-322 2977 is-8 ta-323 sp-8 an-323 2978 is-8 ta-324 sp-8 an-324 2979 is-8 ta-325 sp-8 an-325 2980 is-8 ta-326 sp-8 an-326 2981 is-8 ta-327 sp-8 an-327 2982 is-8 ta-328 sp-8 an-328 2983 is-8 ta-329 sp-8 an-329 2984 is-8 ta-330 sp-8 an-330 2985 is-8 ta-331 sp-8 an-331 2986 is-8 ta-332 sp-8 an-332 2987 is-8 ta-333 sp-8 an-333 2988 is-8 ta-334 sp-8 an-334 2989 is-8 ta-335 sp-8 an-335 2990 is-8 ta-336 sp-8 an-336 2991 is-8 ta-337 sp-8 an-337 2992 is-8 ta-338 sp-8 an-338 2993 is-8 ta-339 sp-8 an-339 2994 is-8 ta-340 sp-8 an-340 2995 is-8 ta-341 sp-8 an-341 2996 is-8 ta-342 sp-8 an-342 2997 is-8 ta-343 sp-8 an-343 2998 is-8 ta-344 sp-8 an-344 2999 is-8 ta-345 sp-8 an-345 3000 is-8 ta-346 sp-8 an-346 3001 is-8 ta-347 sp-8 an-347 3002 is-8 ta-348 sp-8 an-348 3003 is-8 ta-349 sp-8 an-349 3004 is-8 ta-350 sp-8 an-350 3005 is-8 ta-351 sp-8 an-351 3006 is-8 ta-352 sp-8 an-352 3007 is-8 ta-353 sp-8 an-353 3008 is-8 ta-354 sp-8 an-354 3009 is-8 ta-355 sp-8 an-355 3010 is-8 ta-356 sp-8 an-356 3011 is-8 ta-357 sp-8 an-357 3012 is-8 ta-358 sp-8 an-358 3013 is-8 ta-359 sp-8 an-359 3014 is-8 ta-360 sp-8 an-360 3015 is-8 ta-361 sp-8 an-361 3016 is-8 ta-362 sp-8 an-362 3017 is-8 ta-363 sp-8 an-363 3018 is-8 ta-364 sp-8 an-364 3019 is-8 ta-365 sp-8 an-365 3020 is-8 ta-366 sp-8 an-366 3021 is-8 ta-367 sp-8 an-367 3022 is-8 ta-368 sp-8 an-368 3023 is-8 ta-369 sp-8 an-369 3024 is-8 ta-370 sp-8 an-370 3025 is-8 ta-371 sp-8 an-371 3026 is-3 ta-372 sp-8 an-372 3027 is-8 ta-373 sp-8 an-373 3028 is-8 ta-374 sp-8 an-374 3029 is-8 ta-375 sp-8 an-375 3030 is-8 ta-376 sp-8 an-376 3031 is-8 ta-377 sp-8 an-377 3032 is-9 ta-1 sp-9 an-1 3033 is-9 ta-2 sp-9 an-2 3034 is-9 ta-3 sp-9 an-3 3035 is-9 ta-4 sp-9 an-4 3036 is-9 ta-5 sp-9 an-5 3037 is-9 ta-6 sp-9 an-6 3038 is-9 ta-7 sp-9 an-7 3039 is-9 ta-8 sp-9 an-8 3040 is-9 ta-9 sp-9 an-9 3041 is-9 ta-10 sp-9 an-10 3042 is-9 ta-11 sp-9 an-11 3043 is-9 ta-12 sp-9 an-12 3044 is-9 ta-13 sp-9 an-13 3045 is-9 ta-14 sp-9 an-14 3046 is-9 ta-15 sp-9 an-15 3047 is-9 ta-16 sp-9 an-16 3048 is-9 ta-17 sp-9 an-17 3049 is-9 ta-18 sp-9 an-18 3050 is-9 ta-19 sp-9 an-19 3051 is-9 ta-20 sp-9 an-20 3052 is-9 ta-21 sp-9 an-21 3053 is-9 ta-22 sp-9 an-22 3054 is-9 ta-23 sp-9 an-23 3055 is-9 ta-24 sp-9 an-24 3056 is-9 ta-25 sp-9 an-25 3057 is-9 ta-26 sp-9 an-26 3058 is-9 ta-27 sp-9 an-27 3059 is-9 ta-28 sp-9 an-28 3060 is-9 ta-29 sp-9 an-29 3061 is-9 ta-30 sp-9 an-30 3062 is-9 ta-31 sp-9 an-31 3063 is-9 ta-32 sp-9 an-32 3064 is-9 ta-33 sp-9 an-33 3065 is-9 ta-34 sp-9 an-34 3066 is-9 ta-35 sp-9 an-35 3067 is-9 ta-36 sp-9 an-36 3068 is-9 ta-37 sp-9 an-37 3069 is-9 ta-38 sp-9 an-38 3070 is-9 ta-39 sp-9 an-39 3071 is-9 ta-40 sp-9 an-40 3072 is-9 ta-41 sp-9 an-41 3073 is-9 ta-42 sp-9 an-42 3074 is-9 ta-43 sp-9 an-43 3075 is-9 ta-44 sp-9 an-44 3076 is-9 ta-45 sp-9 an-45 3077 is-9 ta-46 sp-9 an-46 3078 is-9 ta-47 sp-9 an-47 3079 is-9 ta-48 sp-9 an-48 3080 is-9 ta-49 sp-9 an-49 3081 is-9 ta-50 sp-9 an-50 3082 is-9 ta-51 sp-9 an-51 3083 is-9 ta-52 sp-9 an-52 3084 is-9 ta-53 sp-9 an-53 3085 is-9 ta-54 sp-9 an-54 3086 is-9 ta-55 sp-9 an-55 3087 is-9 ta-56 sp-9 an-56 3088 is-9 ta-57 sp-9 an-57 3089 is-9 ta-58 sp-9 an-58 3090 is-9 ta-59 sp-9 an-59 3091 is-9 ta-60 sp-9 an-60 3092 is-9 ta-61 sp-9 an-61 3093 is-9 ta-62 sp-9 an-62 3094 is-9 ta-63 sp-9 an-63 3095 is-9 ta-64 sp-9 an-64 3096 is-9 ta-65 sp-9 an-65 3097 is-9 ta-66 sp-9 an-66 3098 is-9 ta-67 sp-9 an-67 3099 is-9 ta-68 sp-9 an-68 3100 is-9 ta-69 sp-9 an-69 3101 is-9 ta-70 sp-9 an-70 3102 is-9 ta-71 sp-9 an-71 3103 is-9 ta-72 sp-9 an-72 3104 is-9 ta-73 sp-9 an-73 3105 is-9 ta-74 sp-9 an-74 3106 is-9 ta-75 sp-9 an-75 3107 is-9 ta-76 sp-9 an-76 3108 is-9 ta-77 sp-9 an-77 3109 is-9 ta-78 sp-9 an-78 3110 is-9 ta-79 sp-9 an-79 3111 is-9 ta-80 sp-9 an-80 3112 is-9 ta-81 sp-9 an-81 3113 is-9 ta-82 sp-9 an-82 3114 is-9 ta-83 sp-9 an-83 3115 is-9 ta-84 sp-9 an-84 3116 is-9 ta-85 sp-9 an-85 3117 is-9 ta-86 sp-9 an-86 3118 is-9 ta-87 sp-9 an-87 3119 is-9 ta-88 sp-9 an-88 3120 is-9 ta-89 sp-9 an-89 3121 is-9 ta-90 sp-9 an-90 3122 is-9 ta-91 sp-9 an-91 3123 is-9 ta-92 sp-9 an-92 3124 is-9 ta-93 sp-9 an-93 3125 is-9 ta-94 sp-9 an-94 3126 is-9 ta-95 sp-9 an-95 3127 is-9 ta-96 sp-9 an-96 3128 is-9 ta-97 sp-9 an-97 3129 is-9 ta-98 sp-9 an-98 3130 is-9 ta-99 sp-9 an-99 3131 is-9 ta-100 sp-9 an-100 3132 is-9 ta-101 sp-9 an-101 3133 is-9 ta-102 sp-9 an-102 3134 is-9 ta-103 sp-9 an-103 3135 is-9 ta-104 sp-9 an-104 3136 is-9 ta-105 sp-9 an-105 3137 is-9 ta-106 sp-9 an-106 3138 is-9 ta-107 sp-9 an-107 3139 is-9 ta-108 sp-9 an-108 3140 is-9 ta-109 sp-9 an-109 3141 is-9 ta-110 sp-9 an-110 3142 is-9 ta-111 sp-9 an-111 3143 is-9 ta-112 sp-9 an-112 3144 is-9 ta-113 sp-9 an-113 3145 is-9 ta-114 sp-9 an-114 3146 is-9 ta-115 sp-9 an-115 3147 is-9 ta-116 sp-9 an-116 3148 is-9 ta-117 sp-9 an-117 3149 is-9 ta-118 sp-9 an-118 3150 is-9 ta-119 sp-9 an-119 3151 is-9 ta-120 sp-9 an-120 3152 is-9 ta-121 sp-9 an-121 3153 is-9 ta-122 sp-9 an-122 3154 is-9 ta-123 sp-9 an-123 3155 is-9 ta-124 sp-9 an-124 3156 is-9 ta-125 sp-9 an-125 3157 is-9 ta-126 sp-9 an-126 3158 is-9 ta-127 sp-9 an-127 3159 is-9 ta-128 sp-9 an-128 3160 is-9 ta-129 sp-9 an-129 3161 is-9 ta-130 sp-9 an-130 3162 is-9 ta-131 sp-9 an-131 3163 is-9 ta-132 sp-9 an-132 3164 is-9 ta-133 sp-9 an-133 3165 is-9 ta-134 sp-9 an-134 3166 is-9 ta-135 sp-9 an-135 3167 is-9 ta-136 sp-9 an-136 3168 is-9 ta-137 sp-9 an-137 3169 is-9 ta-138 sp-9 an-138 3170 is-9 ta-139 sp-9 an-139 3171 is-9 ta-140 sp-9 an-140 3172 is-9 ta-141 sp-9 an-141 3173 is-9 ta-142 sp-9 an-142 3174 is-9 ta-143 sp-9 an-143 3175 is-9 ta-144 sp-9 an-144 3176 is-9 ta-145 sp-9 an-145 3177 is-9 ta-146 sp-9 an-146 3178 is-9 ta-147 sp-9 an-147 3179 is-9 ta-148 sp-9 an-148 3180 is-9 ta-149 sp-9 an-149 3181 is-9 ta-150 sp-9 an-150 3182 is-9 ta-151 sp-9 an-151 3183 is-9 ta-152 sp-9 an-152 3184 is-9 ta-153 sp-9 an-153 3185 is-9 ta-154 sp-9 an-154 3186 is-9 ta-155 sp-9 an-155 3187 is-9 ta-156 sp-9 an-156 3188 is-9 ta-157 sp-9 an-157 3189 is-9 ta-158 sp-9 an-158 3190 is-9 ta-159 sp-9 an-159 3191 is-9 ta-160 sp-9 an-160 3192 is-9 ta-161 sp-9 an-161 3193 is-9 ta-162 sp-9 an-162 3194 is-9 ta-163 sp-9 an-163 3195 is-9 ta-164 sp-9 an-164 3196 is-9 ta-165 sp-9 an-165 3197 is-9 ta-166 sp-9 an-166 3198 is-9 ta-167 sp-9 an-167 3199 is-9 ta-168 sp-9 an-168 3200 is-9 ta-169 sp-9 an-169 3201 is-9 ta-170 sp-9 an-170 3202 is-9 ta-171 sp-9 an-171 3203 is-9 ta-172 sp-9 an-172 3204 is-9 ta-173 sp-9 an-173 3205 is-9 ta-174 sp-9 an-174 3206 is-9 ta-175 sp-9 an-175 3207 is-9 ta-176 sp-9 an-176 3208 is-9 ta-177 sp-9 an-177 3209 is-9 ta-178 sp-9 an-178 3210 is-9 ta-179 sp-9 an-179 3211 is-9 ta-180 sp-9 an-180 3212 is-9 ta-181 sp-9 an-181 3213 is-9 ta-182 sp-9 an-182 3214 is-9 ta-183 sp-9 an-183 3215 is-9 ta-184 sp-9 an-184 3216 is-9 ta-185 sp-9 an-185 3217 is-9 ta-186 sp-9 an-186 3218 is-9 ta-187 sp-9 an-187 3219 is-9 ta-188 sp-9 an-188 3220 is-9 ta-189 sp-9 an-189 3221 is-9 ta-190 sp-9 an-190 3222 is-9 ta-191 sp-9 an-191 3223 is-9 ta-192 sp-9 an-192 3224 is-9 ta-193 sp-9 an-193 3225 is-9 ta-194 sp-9 an-194 3226 is-9 ta-195 sp-9 an-195 3227 is-9 ta-196 sp-9 an-196 3228 is-9 ta-197 sp-9 an-197 3229 is-9 ta-198 sp-9 an-198 3230 is-9 ta-199 sp-9 an-199 3231 is-9 ta-200 sp-9 an-200 3232 is-9 ta-201 sp-9 an-201 3233 is-9 ta-202 sp-9 an-202 3234 is-9 ta-203 sp-9 an-203 3235 is-9 ta-204 sp-9 an-204 3236 is-9 ta-205 sp-9 an-205 3237 is-9 ta-206 sp-9 an-206 3238 is-9 ta-207 sp-9 an-207 3239 is-9 ta-208 sp-9 an-208 3240 is-9 ta-209 sp-9 an-209 3241 is-9 ta-210 sp-9 an-210 3242 is-9 ta-211 sp-9 an-211 3243 is-9 ta-212 sp-9 an-212 3244 is-9 ta-213 sp-9 an-213 3245 is-9 ta-214 sp-9 an-214 3246 is-9 ta-215 sp-9 an-215 3247 is-9 ta-216 sp-9 an-216 3248 is-9 ta-217 sp-9 an-217 3249 is-9 ta-218 sp-9 an-218 3250 is-9 ta-219 sp-9 an-219 3251 is-9 ta-220 sp-9 an-220 3252 is-9 ta-221 sp-9 an-221 3253 is-9 ta-222 sp-9 an-222 3254 is-9 ta-223 sp-9 an-223 3255 is-9 ta-224 sp-9 an-224 3256 is-9 ta-225 sp-9 an-225 3257 is-9 ta-226 sp-9 an-226 3258 is-9 ta-227 sp-9 an-227 3259 is-9 ta-228 sp-9 an-228 3260 is-9 ta-229 sp-9 an-229 3261 is-9 ta-230 sp-9 an-230 3262 is-9 ta-231 sp-9 an-231 3263 is-9 ta-232 sp-9 an-232 3264 is-9 ta-233 sp-9 an-233 3265 is-9 ta-234 sp-9 an-234 3266 is-9 ta-235 sp-9 an-235 3267 is-9 ta-236 sp-9 an-236 3268 is-9 ta-237 sp-9 an-237 3269 is-9 ta-238 sp-9 an-238 3270 is-9 ta-239 sp-9 an-239 3271 is-9 ta-240 sp-9 an-240 3272 is-9 ta-241 sp-9 an-241 3273 is-9 ta-242 sp-9 an-242 3274 is-9 ta-243 sp-9 an-243 3275 is-9 ta-244 sp-9 an-244 3276 is-9 ta-245 sp-9 an-245 3277 is-9 ta-246 sp-9 an-246 3278 is-9 ta-247 sp-9 an-247 3279 is-9 ta-248 sp-9 an-248 3280 is-9 ta-249 sp-9 an-249 3281 is-9 ta-250 sp-9 an-250 3282 is-9 ta-251 sp-9 an-251 3283 is-9 ta-252 sp-9 an-252 3284 is-9 ta-253 sp-9 an-253 3285 is-9 ta-254 sp-9 an-254 3286 is-9 ta-255 sp-9 an-255 3287 is-9 ta-256 sp-9 an-256 3288 is-9 ta-257 sp-9 an-257 3289 is-9 ta-258 sp-9 an-258 3290 is-9 ta-259 sp-9 an-259 3291 is-9 ta-260 sp-9 an-260 3292 is-9 ta-261 sp-9 an-261 3293 is-9 ta-262 sp-9 an-262 3294 is-9 ta-263 sp-9 an-263 3295 is-9 ta-264 sp-9 an-264 3296 is-9 ta-265 sp-9 an-265 3297 is-9 ta-266 sp-9 an-266 3298 is-9 ta-267 sp-9 an-267 3299 is-9 ta-268 sp-9 an-268 3300 is-9 ta-269 sp-9 an-269 3301 is-9 ta-270 sp-9 an-270 3302 is-9 ta-271 sp-9 an-271 3303 is-9 ta-272 sp-9 an-272 3304 is-9 ta-273 sp-9 an-273 3305 is-9 ta-274 sp-9 an-274 3306 is-9 ta-275 sp-9 an-275 3307 is-9 ta-276 sp-9 an-276 3308 is-9 ta-277 sp-9 an-277 3309 is-9 ta-278 sp-9 an-273 3310 is-9 ta-279 sp-9 an-279 3311 is-9 ta-280 sp-9 an-280 3312 is-9 ta-281 sp-9 an-281 3313 is-9 ta-282 sp-9 an-282 3314 is-9 ta-283 sp-9 an-283 3315 is-9 ta-284 sp-9 an-284 3316 is-9 ta-285 sp-9 an-285 3317 is-9 ta-286 sp-9 an-286 3318 is-9 ta-287 sp-9 an-287 3319 is-9 ta-288 sp-9 an-288 3320 is-9 ta-289 sp-9 an-289 3321 is-9 ta-290 sp-9 an-290 3322 is-9 ta-291 sp-9 an-291 3323 is-9 ta-292 sp-9 an-292 3324 is-9 ta-293 sp-9 an-293 3325 is-9 ta-294 sp-9 an-294 3326 is-9 ta-295 sp-9 an-295 3327 is-9 ta-296 sp-9 an-296 3328 is-9 ta-297 sp-9 an-297 3329 is-9 ta-298 sp-9 an-298 3330 is-9 ta-299 sp-9 an-299 3331 is-9 ta-300 sp-9 an-300 3332 is-9 ta-301 sp-9 an-301 3333 is-9 ta-302 sp-9 an-302 3334 is-9 ta-303 sp-9 an-303 3335 is-9 ta-304 sp-9 an-304 3336 is-9 ta-305 sp-9 an-305 3337 is-9 ta-306 sp-9 an-306 3338 is-9 ta-307 sp-9 an-307 3339 is-9 ta-308 sp-9 an-308 3340 is-9 ta-309 sp-9 an-309 3341 is-9 ta-310 sp-9 an-310 3342 is-9 ta-311 sp-9 an-311 3343 is-9 ta-312 sp-9 an-312 3344 is-9 ta-313 sp-9 an-313 3345 is-9 ta-314 sp-9 an-314 3346 is-9 ta-315 sp-9 an-315 3347 is-9 ta-316 sp-9 an-316 3348 is-9 ta-317 sp-9 an-317 3349 is-9 ta-318 sp-9 an-318 3350 is-9 ta-319 sp-9 an-319 3351 is-9 ta-320 sp-9 an-320 3352 is-9 ta-321 sp-9 an-321 3353 is-9 ta-322 sp-9 an-322 3354 is-9 ta-323 sp-9 an-323 3355 is-9 ta-324 sp-9 an-324 3356 is-9 ta-325 sp-9 an-325 3357 is-9 ta-326 sp-9 an-326 3358 is-9 ta-327 sp-9 an-327 3359 is-9 ta-328 sp-9 an-328 3360 is-9 ta-329 sp-9 an-329 3361 is-9 ta-330 sp-9 an-330 3362 is-9 ta-331 sp-9 an-331 3363 is-9 ta-332 sp-9 an-332 3364 is-9 ta-333 sp-9 an-333 3365 is-9 ta-334 sp-9 an-334 3366 is-9 ta-335 sp-9 an-335 3367 is-9 ta-336 sp-9 an-336 3368 is-9 ta-337 sp-9 an-337 3369 is-9 ta-338 sp-9 an-338 3370 is-9 ta-339 sp-9 an-339 3371 is-9 ta-340 sp-9 an-340 3372 is-9 ta-341 sp-9 an-341 3373 is-9 ta-342 sp-9 an-342 3374 is-9 ta-343 sp-9 an-343 3375 is-9 ta-344 sp-9 an-344 3376 is-9 ta-345 sp-9 an-345 3377 is-9 ta-346 sp-9 an-346 3378 is-9 ta-347 sp-9 an-347 3379 is-9 ta-348 sp-9 an-348 3380 is-9 ta-349 sp-9 an-349 3381 is-9 ta-350 sp-9 an-350 3382 is-9 ta-351 sp-9 an-351 3383 is-9 ta-352 sp-9 an-352 3384 is-9 ta-353 sp-9 an-353 3385 is-9 ta-354 sp-9 an-354 3386 is-9 ta-355 sp-9 an-355 3387 is-9 ta-356 sp-9 an-356 3388 is-9 ta-357 sp-9 an-357 3389 is-9 ta-358 sp-9 an-358 3390 is-9 ta-359 sp-9 an-359 3391 is-9 ta-360 sp-9 an-360 3392 is-9 ta-361 sp-9 an-361 3393 is-9 ta-362 sp-9 an-362 3394 is-9 ta-363 sp-9 an-363 3395 is-9 ta-364 sp-9 an-364 3396 is-9 ta-365 sp-9 an-365 3397 is-9 ta-366 sp-9 an-366 3398 is-9 ta-367 sp-9 an-367 3399 is-9 ta-368 sp-9 an-368 3400 is-9 ta-369 sp-9 an-369 3401 is-9 ta-370 sp-9 an-370 3402 is-9 ta-371 sp-9 an-371 3403 is-9 ta-372 sp-9 an-372 3404 is-9 ta-373 sp-9 an-373 3405 is-9 ta-374 sp-9 an-374 3406 is-9 ta-375 sp-9 an-375 3407 is-9 ta-376 sp-9 an-376 3408 is-9 ta-377 sp-9 an-377 3409 is-14 ta-1 sp-14 an-1 3410 is-14 ta-2 sp-14 an-2 3411 is-14 ta-3 sp-14 an-3 3412 is-14 ta-4 sp-14 an-4 3413 is-14 ta-5 sp-14 an-5 3414 is-14 ta-6 sp-14 an-6 3415 is-14 ta-7 sp-14 an-7 3416 is-14 ta-8 sp-14 an-8 3417 is-14 ta-9 sp-14 an-9 3418 is-14 ta-10 sp-14 an-10 3419 is-14 ta-11 sp-14 an-11 3420 is-14 ta-12 sp-14 an-12 3421 is-14 ta-13 sp-14 an-13 3422 is-14 ta-14 sp-14 an-14 3423 is-14 ta-15 sp-14 an-15 3424 is-14 ta-16 sp-14 an-16 3425 is-14 ta-17 sp-14 an-17 3426 is-14 ta-18 sp-14 an-18 3427 is-14 ta-19 sp-14 an-19 3428 is-14 ta-20 sp-14 an-20 3429 is-14 ta-21 sp-14 an-21 3430 is-14 ta-22 sp-14 an-22 3431 is-14 ta-23 sp-14 an-23 3432 is-14 ta-24 sp-14 an-24 3433 is-14 ta-25 sp-14 an-25 3434 is-14 ta-26 sp-14 an-26 3435 is-14 ta-27 sp-14 an-27 3436 is-14 ta-28 sp-14 an-28 3437 is-14 ta-29 sp-14 an-29 3438 is-14 ta-30 sp-14 an-30 3439 is-14 ta-31 sp-14 an-31 3440 is-14 ta-32 sp-14 an-32 3441 is-14 ta-33 sp-14 an-33 3442 is-14 ta-34 sp-14 an-34 3443 is-14 ta-35 sp-14 an-35 3444 is-14 ta-36 sp-14 an-36 3445 is-14 ta-37 sp-14 an-37 3446 is-14 ta-38 sp-14 an-38 3447 is-14 ta-39 sp-14 an-39 3448 is-14 ta-40 sp-14 an-40 3449 is-14 ta-41 sp-14 an-41 3450 is-14 ta-42 sp-14 an-42 3451 is-14 ta-43 sp-14 an-43 3452 is-14 ta-44 sp-14 an-44 3453 is-14 ta-45 sp-14 an-45 3454 is-14 ta-46 sp-14 an-46 3455 is-14 ta-47 sp-14 an-47 3456 is-14 ta-48 sp-14 an-48 3457 is-14 ta-49 sp-14 an-49 3458 is-14 ta-50 sp-14 an-50 3459 is-14 ta-51 sp-14 an-51 3460 is-14 ta-52 sp-14 an-52 3461 is-14 ta-53 sp-14 an-53 3462 is-14 ta-54 sp-14 an-54 3463 is-14 ta-55 sp-14 an-55 3464 is-14 ta-56 sp-14 an-56 3465 is-14 ta-57 sp-14 an-57 3466 is-14 ta-58 sp-14 an-58 3467 is-14 ta-59 sp-14 an-59 3468 is-14 ta-60 sp-14 an-60 3469 is-14 ta-61 sp-14 an-61 3470 is-14 ta-62 sp-14 an-62 3471 is-14 ta-63 sp-14 an-63 3472 is-14 ta-64 sp-14 an-64 3473 is-14 ta-65 sp-14 an-65 3474 is-14 ta-66 sp-14 an-66 3475 is-14 ta-67 sp-14 an-67 3476 is-14 ta-68 sp-14 an-68 3477 is-14 ta-69 sp-14 an-69 3478 is-14 ta-70 sp-14 an-70 3479 is-14 ta-71 sp-14 an-71 3480 is-14 ta-72 sp-14 an-72 3481 is-14 ta-73 sp-14 an-73 3482 is-14 ta-74 sp-14 an-74 3483 is-14 ta-75 sp-14 an-75 3484 is-14 ta-76 sp-14 an-76 3485 is-14 ta-77 sp-14 an-77 3486 is-14 ta-78 sp-14 an-78 3487 is-14 ta-79 sp-14 an-79 3488 is-14 ta-80 sp-14 an-80 3489 is-14 ta-81 sp-14 an-81 3490 is-14 ta-82 sp-14 an-82 3491 is-14 ta-83 sp-14 an-83 3492 is-14 ta-84 sp-14 an-84 3493 is-14 ta-85 sp-14 an-85 3494 is-14 ta-86 sp-14 an-86 3495 is-14 ta-87 sp-14 an-87 3496 is-14 ta-88 sp-14 an-88 3497 is-14 ta-89 sp-14 an-89 3498 is-14 ta-90 sp-14 an-90 3499 is-14 ta-91 sp-14 an-91 3500 is-14 ta-92 sp-14 an-92 3501 is-14 ta-93 sp-14 an-93 3502 is-14 ta-94 sp-14 an-94 3503 is-14 ta-95 sp-14 an-95 3504 is-14 ta-96 sp-14 an-96 3505 is-14 ta-97 sp-14 an-97 3506 is-14 ta-98 sp-14 an-98 3507 is-14 ta-99 sp-14 an-99 3508 is-14 ta-100 sp-14 an-100 3509 is-14 ta-101 sp-14 an-101 3510 is-14 ta-102 sp-14 an-102 3511 is-14 ta-103 sp-14 an-103 3512 is-14 ta-104 sp-14 an-104 3513 is-14 ta-105 sp-14 an-105 3514 is-14 ta-106 sp-14 an-106 3515 is-14 ta-107 sp-14 an-107 3516 is-14 ta-108 sp-14 an-108 3517 is-14 ta-109 sp-14 an-109 3518 is-14 ta-110 sp-14 an-110 3519 is-14 ta-111 sp-14 an-111 3520 is-14 ta-112 sp-14 an-112 3521 is-14 ta-113 sp-14 an-113 3522 is-14 ta-114 sp-14 an-114 3523 is-14 ta-115 sp-14 an-115 3524 is-14 ta-116 sp-14 an-116 3525 is-14 ta-117 sp-14 an-117 3526 is-14 ta-118 sp-14 an-118 3527 is-14 ta-119 sp-14 an-119 3528 is-14 ta-120 sp-14 an-120 3529 is-14 ta-121 sp-14 an-121 3530 is-14 ta-122 sp-14 an-122 3531 is-14 ta-123 sp-14 an-123 3532 is-14 ta-124 sp-14 an-124 3533 is-14 ta-125 sp-14 an-125 3534 is-14 ta-126 sp-14 an-126 3535 is-14 ta-127 sp-14 an-127 3536 is-14 ta-128 sp-14 an-128 3537 is-14 ta-129 sp-14 an-129 3538 is-14 ta-130 sp-14 an-130 3539 is-14 ta-131 sp-14 an-131 3540 is-14 ta-132 sp-14 an-132 3541 is-14 ta-133 sp-14 an-133 3542 is-14 ta-134 sp-14 an-134 3543 is-14 ta-135 sp-14 an-135 3544 is-14 ta-136 sp-14 an-136 3545 is-14 ta-137 sp-14 an-137 3546 is-14 ta-138 sp-14 an-138 3547 is-14 ta-139 sp-14 an-139 3548 is-14 ta-140 sp-14 an-140 3549 is-14 ta-141 sp-14 an-141 3550 is-14 ta-142 sp-14 an-142 3551 is-14 ta-143 sp-14 an-143 3552 is-14 ta-144 sp-14 an-144 3553 is-14 ta-145 sp-14 an-145 3554 is-14 ta-146 sp-14 an-146 3555 is-14 ta-147 sp-14 an-147 3556 is-14 ta-148 sp-14 an-148 3557 is-14 ta-149 sp-14 an-149 3558 is-14 ta-150 sp-14 an-150 3559 is-14 ta-151 sp-14 an-151 3560 is-14 ta-152 sp-14 an-152 3561 is-14 ta-153 sp-14 an-153 3562 is-14 ta-154 sp-14 an-154 3563 is-14 ta-155 sp-14 an-155 3564 is-14 ta-156 sp-14 an-156 3565 is-14 ta-157 sp-14 an-157 3566 is-14 ta-158 sp-14 an-158 3567 is-14 ta-159 sp-14 an-159 3568 is-14 ta-160 sp-14 an-160 3569 is-14 ta-161 sp-14 an-161 3570 is-14 ta-162 sp-14 an-162 3571 is-14 ta-163 sp-14 an-163 3572 is-14 ta-164 sp-14 an-164 3573 is-14 ta-165 sp-14 an-165 3574 is-14 ta-166 sp-14 an-166 3575 is-14 ta-167 sp-14 an-167 3576 is-14 ta-168 sp-14 an-168 3577 is-14 ta-169 sp-14 an-169 3578 is-14 ta-170 sp-14 an-170 3579 is-14 ta-171 sp-14 an-171 3580 is-14 ta-172 sp-14 an-172 3581 is-14 ta-173 sp-14 an-173 3582 is-14 ta-174 sp-14 an-174 3583 is-14 ta-175 sp-14 an-175 3584 is-14 ta-176 sp-14 an-176 3585 is-14 ta-177 sp-14 an-177 3586 is-14 ta-178 sp-14 an-178 3587 is-14 ta-179 sp-14 an-179 3588 is-14 ta-180 sp-14 an-180 3589 is-14 ta-181 sp-14 an-181 3590 is-14 ta-182 sp-14 an-182 3591 is-14 ta-183 sp-14 an-183 3592 is-14 ta-184 sp-14 an-184 3593 is-14 ta-185 sp-14 an-185 3594 is-14 ta-186 sp-14 an-186 3595 is-14 ta-187 sp-14 an-187 3596 is-14 ta-188 sp-14 an-188 3597 is-14 ta-189 sp-14 an-189 3598 is-14 ta-190 sp-14 an-190 3599 is-14 ta-191 sp-14 an-191 3600 is-14 ta-192 sp-14 an-192 3601 is-14 ta-193 sp-14 an-193 3602 is-14 ta-194 sp-14 an-194 3603 is-14 ta-195 sp-14 an-195 3604 is-14 ta-196 sp-14 an-196 3605 is-14 ta-197 sp-14 an-197 3606 is-14 ta-198 sp-14 an-198 3607 is-14 ta-199 sp-14 an-199 3608 is-14 ta-200 sp-14 an-200 3609 is-14 ta-201 sp-14 an-201 3610 is-14 ta-202 sp-14 an-202 3611 is-14 ta-203 sp-14 an-203 3612 is-14 ta-204 sp-14 an-204 3613 is-14 ta-205 sp-14 an-205 3614 is-14 ta-206 sp-14 an-206 3615 is-14 ta-207 sp-14 an-207 3616 is-14 ta-208 sp-14 an-208 3617 is-14 ta-209 sp-14 an-209 3618 is-14 ta-210 sp-14 an-210 3619 is-14 ta-211 sp-14 an-211 3620 is-14 ta-212 sp-14 an-212 3621 is-14 ta-213 sp-14 an-213 3622 is-14 ta-214 sp-14 an-214 3623 is-14 ta-215 sp-14 an-215 3624 is-14 ta-216 sp-14 an-216 3625 is-14 ta-217 sp-14 an-217 3626 is-14 ta-218 sp-14 an-218 3627 is-14 ta-219 sp-14 an-219 3628 is-14 ta-220 sp-14 an-220 3629 is-14 ta-221 sp-14 an-221 3630 is-14 ta-222 sp-14 an-222 3631 is-14 ta-223 sp-14 an-223 3632 is-14 ta-224 sp-14 an-224 3633 is-14 ta-225 sp-14 an-225 3634 is-14 ta-226 sp-14 an-226 3635 is-14 ta-227 sp-14 an-227 3636 is-14 ta-228 sp-14 an-228 3637 is-14 ta-229 sp-14 an-229 3638 is-14 ta-230 sp-14 an-230 3639 is-14 ta-231 sp-14 an-231 3640 is-14 ta-232 sp-14 an-232 3641 is-14 ta-233 sp-14 an-233 3642 is-14 ta-234 sp-14 an-234 3643 is-14 ta-235 sp-14 an-235 3644 is-14 ta-236 sp-14 an-236 3645 is-14 ta-237 sp-14 an-237 3646 is-14 ta-238 sp-14 an-238 3647 is-14 ta-239 sp-14 an-239 3648 is-14 ta-240 sp-14 an-240 3649 is-14 ta-241 sp-14 an-241 3650 is-14 ta-242 sp-14 an-242 3651 is-14 ta-243 sp-14 an-243 3652 is-14 ta-244 sp-14 an-244 3653 is-14 ta-245 sp-14 an-245 3654 is-14 ta-246 sp-14 an-246 3655 is-14 ta-247 sp-14 an-247 3656 is-14 ta-248 sp-14 an-248 3657 is-14 ta-249 sp-14 an-249 3658 is-14 ta-250 sp-14 an-250 3659 is-14 ta-251 sp-14 an-251 3660 is-14 ta-252 sp-14 an-252 3661 is-14 ta-253 sp-14 an-253 3662 is-14 ta-254 sp-14 an-254 3663 is-14 ta-255 sp-14 an-255 3664 is-14 ta-256 sp-14 an-256 3665 is-14 ta-257 sp-14 an-257 3666 is-14 ta-258 sp-14 an-258 3667 is-14 ta-259 sp-14 an-259 3668 is-14 ta-260 sp-14 an-260 3669 is-14 ta-261 sp-14 an-261 3670 is-14 ta-262 sp-14 an-262 3671 is-14 ta-263 sp-14 an-263 3672 is-14 ta-264 sp-14 an-264 3673 is-14 ta-265 sp-14 an-265 3674 is-14 ta-266 sp-14 an-266 3675 is-14 ta-267 sp-14 an-267 3676 is-14 ta-268 sp-14 an-268 3677 is-14 ta-269 sp-14 an-269 3678 is-14 ta-270 sp-14 an-270 3679 is-14 ta-271 sp-14 an-271 3680 is-14 ta-272 sp-14 an-272 3681 is-14 ta-273 sp-14 an-273 3682 is-14 ta-274 sp-14 an-274 3683 is-14 ta-275 sp-14 an-275 3684 is-14 ta-276 sp-14 an-276 3685 is-14 ta-277 sp-14 an-277 3686 is-14 ta-278 sp-14 an-278 3687 is-14 ta-279 sp-14 an-279 3688 is-14 ta-280 sp-14 an-280 3689 is-14 ta-281 sp-14 an-281 3690 is-14 ta-282 sp-14 an-282 3691 is-14 ta-283 sp-14 an-283 3692 is-14 ta-284 sp-14 an-284 3693 is-14 ta-285 sp-14 an-285 3694 is-14 ta-286 sp-14 an-286 3695 is-14 ta-287 sp-14 an-287 3696 is-14 ta-288 sp-14 an-288 3697 is-14 ta-289 sp-14 an-289 3698 is-14 ta-290 sp-14 an-290 3699 is-14 ta-291 sp-14 an-291 3700 is-14 ta-292 sp-14 an-292 3701 is-14 ta-293 sp-14 an-293 3702 is-14 ta-294 sp-14 an-294 3703 is-14 ta-295 sp-14 an-295 3704 is-14 ta-296 sp-14 an-296 3705 is-14 ta-297 sp-14 an-297 3706 is-14 ta-298 sp-14 an-298 3707 is-14 ta-299 sp-14 an-299 3708 is-14 ta-300 sp-14 an-300 3709 is-14 ta-301 sp-14 an-301 3710 is-14 ta-302 sp-14 an-302 3711 is-14 ta-303 sp-14 an-303 3712 is-14 ta-304 sp-14 an-304 3713 is-14 ta-305 sp-14 an-305 3714 is-14 ta-306 sp-14 an-306 3715 is-14 ta-307 sp-14 an-307 3716 is-14 ta-308 sp-14 an-308 3717 is-14 ta-309 sp-14 an-309 3718 is-14 ta-310 sp-14 an-310 3719 is-14 ta-311 sp-14 an-311 3720 is-14 ta-312 sp-14 an-312 3721 is-14 ta-313 sp-14 an-313 3722 is-14 ta-314 sp-14 an-314 3723 is-14 ta-315 sp-14 an-315 3724 is-14 ta-316 sp-14 an-316 3725 is-14 ta-317 sp-14 an-317 3726 is-14 ta-318 sp-14 an-318 3727 is-14 ta-319 sp-14 an-319 3728 is-14 ta-320 sp-14 an-320 3729 is-14 ta-321 sp-14 an-321 3730 is-14 ta-322 sp-14 an-322 3731 is-14 ta-323 sp-14 an-323 3732 is-14 ta-324 sp-14 an-324 3733 is-14 ta-325 sp-14 an-325 3734 is-14 ta-326 sp-14 an-326 3735 is-14 ta-327 sp-14 an-327 3736 is-14 ta-328 sp-14 an-328 3737 is-14 ta-329 sp-14 an-329 3738 is-14 ta-330 sp-14 an-330 3739 is-14 ta-331 sp-14 an-331 3740 is-14 ta-332 sp-14 an-332 3741 is-14 ta-333 sp-14 an-333 3742 is-14 ta-334 sp-14 an-334 3743 is-14 ta-335 sp-14 an-335 3744 is-14 ta-336 sp-14 an-336 3745 is-14 ta-337 sp-14 an-337 3746 is-14 ta-338 sp-14 an-338 3747 is-14 ta-339 sp-14 an-339 3748 is-14 ta-340 sp-14 an-340 3749 is-14 ta-341 sp-14 an-341 3750 is-14 ta-342 sp-14 an-342 3751 is-14 ta-343 sp-14 an-343 3752 is-14 ta-344 sp-14 an-344 3753 is-14 ta-345 sp-14 an-345 3754 is-14 ta-346 sp-14 an-346 3755 is-14 ta-347 sp-14 an-347 3756 is-14 ta-348 sp-14 an-348 3757 is-14 ta-349 sp-14 an-349 3758 is-14 ta-350 sp-14 an-350 3759 is-14 ta-351 sp-14 an-351 3760 is-14 ta-352 sp-14 an-352 3761 is-14 ta-353 sp-14 an-353 3762 is-14 ta-354 sp-14 an-354 3763 is-14 ta-355 sp-14 an-355 3764 is-14 ta-356 sp-14 an-356 3765 is-14 ta-357 sp-14 an-357 3766 is-14 ta-358 sp-14 an-358 3767 is-14 ta-359 sp-14 an-359 3768 is-14 ta-360 sp-14 an-360 3769 is-14 ta-361 sp-14 an-361 3770 is-14 ta-362 sp-14 an-362 3771 is-14 ta-363 sp-14 an-363 3772 is-14 ta-364 sp-14 an-364 3773 is-14 ta-365 sp-14 an-365 3774 is-14 ta-366 sp-14 an-366 3775 is-14 ta-367 sp-14 an-367 3776 is-14 ta-368 sp-14 an-368 3777 is-14 ta-369 sp-14 an-369 3778 is-14 ta-370 sp-14 an-370 3779 is-14 ta-371 sp-14 an-371 3780 is-14 ta-372 sp-14 an-372 3781 is-14 ta-373 sp-14 an-373 3782 is-14 ta-374 sp-14 an-374 3783 is-14 ta-375 sp-14 an-375 3784 is-14 ta-376 sp-14 an-376 3785 is-14 ta-377 sp-14 an-377 End of Table 2

Examples from 3786 to 4064

As shown in the following formulae,

the procedure in the steps n to p in Example 1 is followed except that the compound obtained in the step m in Example 1, any one of the various acyl halides (ac-1) to (ac-17) represented by the formula (5-1), and any one of the various tertiary amines (ta-1) to (ta-377) represented by the formula (2) are used to obtain compounds of Examples 3786 to 4064 as represented by the formula (1B) as shown in Table 3. In the formula (1B), “-sp-” indicates any one of the (sp-1) to (sp-22) described above and “-an” indicates any one of the (an-1) to (an-377) described above. TABLE 3 REACTION COMPOUND OF EX. REAGENT EXAMPLE No. ac ta sp an 3786 ac-3 ta-1 sp-3 an-1 3787 ac-3 ta-2 sp-3 an-2 3788 ac-3 ta-3 sp-3 an-3 3789 ac-3 ta-4 sp-3 an-4 3790 ac-3 ta-5 sp-3 an-5 3791 ac-3 ta-6 sp-3 an-6 3792 ac-3 ta-21 sp-3 an-21 3793 ac-3 ta-25 sp-3 an-25 3794 ac-3 ta-26 sp-3 an-26 3795 ac-3 ta-32 sp-3 an-32 3796 ac-3 ta-34 sp-3 an-34 3797 ac-3 ta-38 sp-3 an-38 3798 ac-3 ta-41 sp-3 an-41 3799 ac-3 ta-42 sp-3 an-42 3800 ac-3 ta-44 sp-3 an-44 3801 ac-3 ta-45 sp-3 an-45 3802 ac-3 ta-47 sp-3 an-47 3803 ac-3 ta-49 sp-3 an-49 3804 ac-3 ta-67 sp-3 an-67 3805 ac-3 ta-88 sp-3 an-88 3806 ac-3 ta-89 sp-3 an-89 3807 ac-3 ta-98 sp-3 an-98 3808 ac-3 ta-99 sp-3 an-99 3809 ac-3 ta-100 sp-3 an-100 3810 ac-3 ta-101 sp-3 an-101 3811 ac-3 ta-107 sp-3 an-107 3812 ac-3 ta-115 sp-3 an-115 3813 ac-3 ta-287 sp-3 an-287 3814 ac-3 ta-288 sp-3 an-288 3815 ac-3 ta-289 sp-3 an-289 3816 ac-3 ta-290 sp-3 an-290 3817 ac-3 ta-291 sp-3 an-291 3818 ac-3 ta-292 sp-3 an-292 3819 ac-3 ta-293 sp-3 an-293 3820 ac-3 ta-294 sp-3 an-294 3821 ac-3 ta-295 sp-3 an-295 3822 ac-3 ta-296 sp-3 an-296 3823 ac-3 ta-297 sp-3 an-297 3824 ac-3 ta-298 sp-3 an-298 3825 ac-3 ta-299 sp-3 an-299 3826 ac-4 ta-1 sp-4 an-1 3827 ac-4 ta-2 sp-4 an-2 3828 ac-4 ta-3 sp-4 an-3 3829 ac-4 ta-4 sp-4 an-4 3830 ac-4 ta-5 sp-4 an-5 3831 ac-4 ta-6 sp-4 an-6 3832 ac-4 ta-21 sp-4 an-21 3833 ac-4 ta-25 sp-4 an-25 3834 ac-4 ta-26 sp-4 an-26 3835 ac-4 ta-32 sp-4 an-32 3836 ac-4 ta-34 sp-4 an-34 3837 ac-4 ta-38 sp-4 an-38 3838 ac-4 ta-41 sp-4 an-41 3839 ac-4 ta-42 sp-4 an-42 3840 ac-4 ta-44 sp-4 an-44 3841 ac-4 ta-45 sp-4 an-45 3842 ac-4 ta-47 sp-4 an-47 3843 ac-4 ta-49 sp-4 an-49 3844 ac-4 ta-67 sp-4 an-67 3845 ac-4 ta-88 sp-4 an-88 3846 ac-4 ta-89 sp-4 an-89 3847 ac-4 ta-98 sp-4 an-98 3848 ac-4 ta-99 sp-4 an-99 3849 ac-4 ta-100 sp-4 an-100 3850 ac-4 ta-101 sp-4 an-101 3851 ac-4 ta-107 sp-4 an-107 3852 ac-4 ta-115 sp-4 an-115 1 ac-4 ta-287 sp-4 an-287 3853 ac-4 ta-288 sp-4 an-288 3854 ac-4 ta-289 sp-4 an-289 3855 ac-4 ta-290 sp-4 an-290 3856 ac-4 ta-291 sp-4 an-291 3857 ac-4 ta-292 sp-4 an-292 3858 ac-4 ta-293 sp-4 an-293 3859 ac-4 ta-294 sp-4 an-294 3860 ac-4 ta-295 sp-4 an-295 3861 ac-4 ta-296 sp-4 an-296 3862 ac-4 ta-297 sp-4 an-297 3863 ac-4 ta-298 sp-4 an-298 3864 ac-4 ta-299 sp-4 an-299 3865 ac-5 ta-1 sp-5 an-1 3866 ac-5 ta-2 sp-5 an-2 3867 ac-5 ta-3 sp-5 an-3 3868 ac-5 ta-4 sp-5 an-4 3869 ac-5 ta-5 sp-5 an-5 3870 ac-5 ta-6 sp-5 an-6 3871 ac-5 ta-21 sp-5 an-21 3872 ac-5 ta-25 sp-5 an-25 3873 ac-5 ta-26 sp-5 an-26 3874 ac-5 ta-32 sp-5 an-32 3875 ac-5 ta-34 sp-5 an-34 3876 ac-5 ta-38 sp-5 an-38 3877 ac-5 ta-41 sp-5 an-41 3878 ac-5 ta-42 sp-5 an-42 3879 ac-5 ta-44 sp-5 an-44 3880 ac-5 ta-45 sp-5 an-45 3881 ac-5 ta-47 sp-5 an-47 3882 ac-5 ta-49 sp-5 an-49 3883 ac-5 ta-67 sp-5 an-67 3884 ac-5 ta-88 sp-5 an-88 3885 ac-5 ta-89 sp-5 an-89 3886 ac-5 ta-98 sp-5 an-98 3887 ac-5 ta-99 sp-5 an-99 3888 ac-5 ta-100 sp-5 an-100 3889 ac-5 ta-101 sp-5 an-101 3890 ac-5 ta-107 sp-5 an-107 3891 ac-5 ta-115 sp-5 an-115 3892 ac-5 ta-287 sp-5 an-287 3893 ac-5 ta-288 sp-5 an-288 3894 ac-5 ta-289 sp-5 an-289 3895 ac-5 ta-290 sp-5 an-290 3896 ac-5 ta-291 sp-5 an-291 3897 ac-5 ta-292 sp-5 an-292 3898 ac-5 ta-293 sp-5 an-293 3899 ac-5 ta-294 sp-5 an-294 3900 ac-5 ta-295 sp-5 an-295 3901 ac-5 ta-296 sp-5 an-296 3902 ac-5 ta-297 sp-5 an-297 3903 ac-5 ta-298 sp-5 an-298 3904 ac-5 ta-299 sp-5 an-299 3905 ac-6 ta-1 sp-6 an-1 3906 ac-6 ta-2 sp-6 an-2 3907 ac-6 ta-3 sp-6 an-3 3908 ac-6 ta-4 sp-6 an-4 3909 ac-6 ta-5 sp-6 an-5 3910 ac-6 ta-6 sp-6 an-6 3911 ac-6 ta-21 sp-6 an-21 3912 ac-6 ta-25 sp-6 an-25 3913 ac-6 ta-26 sp-6 an-26 3914 ac-6 ta-32 sp-6 an-32 3915 ac-6 ta-34 sp-6 an-34 3916 ac-6 ta-38 sp-6 an-38 3917 ac-6 ta-41 sp-6 an-41 3918 ac-6 ta-42 sp-6 an-42 3919 ac-6 ta-44 sp-6 an-44 3920 ac-6 ta-45 sp-6 an-45 3921 ac-6 ta-47 sp-6 an-47 3922 ac-6 ta-49 sp-6 an-49 3923 ac-6 ta-67 sp-6 an-67 3924 ac-6 ta-88 sp-6 an-88 3925 ac-6 ta-89 sp-6 an-89 3926 ac-6 ta-98 sp-6 an-98 3927 ac-6 ta-99 sp-6 an-99 3928 ac-6 ta-100 sp-6 an-100 3929 ac-6 ta-101 sp-6 an-101 3930 ac-6 ta-107 sp-6 an-107 3931 ac-6 ta-115 sp-6 an-115 3932 ac-6 ta-287 sp-6 an-287 3933 ac-6 ta-288 sp-6 an-288 3934 ac-6 ta-289 sp-6 an-289 3935 ac-6 ta-290 sp-6 an-290 3936 ac-6 ta-291 sp-6 an-291 3937 ac-6 ta-292 sp-6 an-292 3938 ac-6 ta-293 sp-6 an-293 3939 ac-6 ta-294 sp-6 an-294 3940 ac-6 ta-295 sp-6 an-295 3941 ac-6 ta-296 sp-6 an-296 3942 ac-6 ta-297 sp-6 an-297 3943 ac-6 ta-298 sp-6 an-298 3944 ac-6 ta-299 sp-6 an-299 3945 ac-7 ta-1 sp-7 an-1 3946 ac-7 ta-2 sp-7 an-2 3947 ac-7 ta-3 sp-7 an-3 3948 ac-7 ta-4 sp-7 an-4 3949 ac-7 ta-5 sp-7 an-5 3950 ac-7 ta-6 sp-7 an-6 3951 ac-7 ta-21 sp-7 an-21 3952 ac-7 ta-25 sp-7 an-25 3953 ac-7 ta-26 sp-7 an-26 3954 ac-7 ta-32 sp-7 an-32 3955 ac-7 ta-34 sp-7 an-34 3956 ac-7 ta-38 sp-7 an-38 3957 ac-7 ta-41 sp-7 an-41 3958 ac-7 ta-42 sp-7 an-42 3959 ac-7 ta-44 sp-7 an-44 3960 ac-7 ta-45 sp-7 an-45 3961 ac-7 ta-47 sp-7 an-47 3962 ac-7 ta-49 sp-7 an-49 3963 ac-7 ta-67 sp-7 an-67 3964 ac-7 ta-88 sp-7 an-88 3965 ac-7 ta-89 sp-7 an-89 3966 ac-7 ta-98 sp-7 an-98 3967 ac-7 ta-99 sp-7 an-99 3968 ac-7 ta-100 sp-7 an-100 3969 ac-7 ta-101 sp-7 an-101 3970 ac-7 ta-107 sp-7 an-107 3971 ac-7 ta-115 sp-7 an-115 3972 ac-7 ta-287 sp-7 an-287 3973 ac-7 ta-288 sp-7 an-288 3974 ac-7 ta-289 sp-7 an-289 3975 ac-7 ta-290 sp-7 an-290 3976 ac-7 ta-291 sp-7 an-291 3977 ac-7 ta-292 sp-7 an-292 3978 ac-7 ta-293 sp-7 an-293 3979 ac-7 ta-294 sp-7 an-294 3980 ac-7 ta-295 sp-7 an-295 3981 ac-7 ta-296 sp-7 an-296 3982 ac-7 ta-297 sp-7 an-297 3983 ac-7 ta-298 sp-7 an-298 3984 ac-7 ta-299 sp-7 an-299 3985 ac-8 ta-1 sp-8 an-1 3986 ac-8 ta-2 sp-8 an-2 3987 ac-8 ta-3 sp-8 an-3 3988 ac-8 ta-4 sp-8 an-4 3989 ac-8 ta-5 sp-8 an-5 3990 ac-8 ta-6 sp-8 an-6 3991 ac-8 ta-21 sp-8 an-21 3992 ac-8 ta-25 sp-8 an-25 3993 ac-8 ta-26 sp-8 an-26 3994 ac-8 ta-32 sp-8 an-32 3995 ac-8 ta-34 sp-8 an-34 3996 ac-8 ta-38 sp-8 an-38 3997 ac-8 ta-41 sp-8 an-41 3998 ac-8 ta-42 sp-8 an-42 3999 ac-8 ta-44 sp-8 an-44 4000 ac-8 ta-45 sp-8 an-45 4001 ac-8 ta-47 sp-8 an-47 4002 ac-8 ta-49 sp-8 an-49 4003 ac-8 ta-67 sp-8 an-67 4004 ac-8 ta-88 sp-8 an-88 4005 ac-8 ta-89 sp-8 an-89 4006 ac-8 ta-98 sp-8 an-98 4007 ac-8 ta-99 sp-8 an-99 4008 ac-8 ta-100 sp-8 an-100 4009 ac-8 ta-101 sp-8 an-101 4010 ac-8 ta-107 sp-8 an-107 4011 ac-8 ta-115 sp-8 an-115 4012 ac-8 ta-287 sp-8 an-287 4013 ac-8 ta-288 sp-8 an-288 4014 ac-8 ta-289 sp-8 an-289 4015 ac-8 ta-290 sp-8 an-290 4016 ac-8 ta-291 sp-8 an-291 4017 ac-8 ta-292 sp-8 an-292 4018 ac-8 ta-293 sp-8 an-293 4019 ac-8 ta-294 sp-8 an-294 4020 ac-8 ta-295 sp-8 an-295 4021 ac-8 ta-296 sp-8 an-296 4022 ac-8 ta-297 sp-8 an-297 4023 ac-8 ta-298 sp-8 an-298 4024 ac-8 ta-299 sp-8 an-299 4025 ac-9 ta-1 sp-9 an-1 4026 ac-9 ta-2 sp-9 an-2 4027 ac-9 ta-3 sp-9 an-3 4028 ac-9 ta-4 sp-9 an-4 4029 ac-9 ta-5 sp-9 an-5 4030 ac-9 ta-6 sp-9 an-6 4031 ac-9 ta-21 sp-9 an-21 4032 ac-9 ta-25 sp-9 an-25 4033 ac-9 ta-26 sp-9 an-26 4034 ac-9 ta-32 sp-9 an-32 4035 ac-9 ta-34 sp-9 an-34 4036 ac-9 ta-38 sp-9 an-38 4037 ac-9 ta-41 sp-9 an-41 4038 ac-9 ta-42 sp-9 an-42 4039 ac-9 ta-44 sp-9 an-44 4040 ac-9 ta-45 sp-9 an-45 4041 ac-9 ta-47 sp-9 an-47 4042 ac-9 ta-49 sp-9 an-49 4043 ac-9 ta-67 sp-9 an-67 4044 ac-9 ta-88 sp-9 an-88 4045 ac-9 ta-89 sp-9 an-89 4046 ac-9 ta-98 sp-9 an-98 4047 ac-9 ta-99 sp-9 an-99 4048 ac-9 ta-100 sp-9 an-100 4049 ac-9 ta-101 sp-9 an-101 4050 ac-9 ta-107 sp-9 an-107 4051 ac-9 ta-115 sp-9 an-115 4052 ac-9 ta-287 sp-9 an-287 4053 ac-9 ta-288 sp-9 an-288 4054 ac-9 ta-289 sp-9 an-289 4055 ac-9 ta-290 sp-9 an-290 4056 ac-9 ta-291 sp-9 an-291 4057 ac-9 ta-292 sp-9 an-292 4058 ac-9 ta-293 sp-9 an-293 4059 ac-9 ta-294 sp-9 an-294 4060 ac-9 ta-295 sp-9 an-295 4061 ac-9 ta-296 sp-9 an-296 4062 ac-9 ta-297 sp-9 an-297 4063 ac-9 ta-298 sp-9 an-298 4064 ac-9 ta-299 sp-9 an-299 3945 ac-7 ta-1 sp-7 an-1 3946 ac-7 ta-2 sp-7 an-2 3947 ac-7 ta-3 sp-7 an-3 3948 ac-7 ta-4 sp-7 an-4 3949 ac-7 ta-5 sp-7 an-5 3950 ac-7 ta-6 sp-7 an-6 3951 ac-7 ta-21 sp-7 an-21 3952 ac-7 ta-25 sp-7 an-25 3953 ac-7 ta-26 sp-7 an-26 3954 ac-7 ta-32 sp-7 an-32 3955 ac-7 ta-34 sp-7 an-34 3956 ac-7 ta-38 sp-7 an-38 3957 ac-7 ta-41 sp-7 an-41 3958 ac-7 ta-42 sp-7 an-42 3959 ac-7 ta-44 sp-7 an-44 3960 ac-7 ta-45 sp-7 an-45 3961 ac-7 ta-47 sp-7 an-47 3962 ac-7 ta-49 sp-7 an-49 3963 ac-7 ta-67 sp-7 an-67 3964 ac-7 ta-88 sp-7 an-88 3965 ac-7 ta-89 sp-7 an-89 3966 ac-7 ta-98 sp-7 an-98 3967 ac-7 ta-99 sp-7 an-99 3968 ac-7 ta-100 sp-7 an-100 3969 ac-7 ta-101 sp-7 an-101 3970 ac-7 ta-107 sp-7 an-107 3971 ac-7 ta-115 sp-7 an-115 3972 ac-7 ta-287 sp-7 an-287 3973 ac-7 ta-288 sp-7 an-288 3974 ac-7 ta-289 sp-7 an-289 3975 ac-7 ta-290 sp-7 an-290 3976 ac-7 ta-291 sp-7 an-291 3977 ac-7 ta-292 sp-7 an-292 3978 ac-7 ta-293 sp-7 an-293 3979 ac-7 ta-294 sp-7 an-294 3980 ac-7 ta-295 sp-7 an-295 3981 ac-7 ta-296 sp-7 an-296 3982 ac-7 ta-297 sp-7 an-297 3983 ac-7 ta-298 sp-7 an-298 3984 ac-7 ta-299 sp-7 an-299 3985 ac-8 ta-1 sp-8 an-1 3986 ac-8 ta-2 sp-8 an-2 3987 ac-8 ta-3 sp-8 an-3 3988 ac-8 ta-4 sp-8 an-4 3989 ac-8 ta-5 sp-8 an-5 3990 ac-8 ta-6 sp-8 an-6 3991 ac-8 ta-21 sp-8 an-21 3992 ac-8 ta-25 sp-8 an-25 3993 ac-8 ta-26 sp-8 an-26 3994 ac-8 ta-32 sp-8 an-32 3995 ac-8 ta-34 sp-8 an-34 3996 ac-8 ta-38 sp-8 an-38 3997 ac-8 ta-41 sp-8 an-41 3998 ac-8 ta-42 sp-8 an-42 3999 ac-8 ta-44 sp-8 an-44 4000 ac-8 ta-45 sp-8 an-45 4001 ac-8 ta-47 sp-8 an-47 4002 ac-8 ta-49 sp-8 an-49 4003 ac-8 ta-67 sp-8 an-67 4004 ac-8 ta-88 sp-8 an-88 4005 ac-8 ta-89 sp-8 an-89 4006 ac-8 ta-98 sp-8 an-98 4007 ac-8 ta-99 sp-8 an-99 4008 ac-8 ta-100 sp-8 an-100 4009 ac-8 ta-101 sp-8 an-101 4010 ac-8 ta-107 sp-8 an-107 4011 ac-8 ta-115 sp-8 an-115 4012 ac-8 ta-287 sp-8 an-287 4013 ac-8 ta-288 sp-8 an-288 4014 ac-8 ta-289 sp-8 an-289 4015 ac-8 ta-290 sp-8 an-290 4016 ac-8 ta-291 sp-8 an-291 4017 ac-8 ta-292 sp-8 an-292 4018 ac-8 ta-293 sp-8 an-293 4019 ac-8 ta-294 sp-8 an-294 4020 ac-8 ta-295 sp-8 an-295 4021 ac-8 ta-296 sp-8 an-296 4022 ac-8 ta-297 sp-8 an-297 4023 ac-8 ta-298 sp-8 an-298 4024 ac-8 ta-299 sp-8 an-299 4025 ac-9 ta-1 sp-9 an-1 4026 ac-9 ta-2 sp-9 an-2 4027 ac-9 ta-3 sp-9 an-3 4028 ac-9 ta-4 sp-9 an-4 4029 ac-9 ta-5 sp-9 an-5 4030 ac-9 ta-6 sp-9 an-6 4031 ac-9 ta-21 sp-9 an-21 4032 ac-9 ta-25 sp-9 an-25 4033 ac-9 ta-26 sp-9 an-26 4034 ac-9 ta-32 sp-9 an-32 4035 ac-9 ta-34 sp-9 an-34 4036 ac-9 ta-38 sp-9 an-38 4037 ac-9 ta-41 sp-9 an-41 4038 ac-9 ta-42 sp-9 an-42 4039 ac-9 ta-44 sp-9 an-44 4040 ac-9 ta-45 sp-9 an-45 4041 ac-9 ta-47 sp-9 an-47 4042 ac-9 ta-49 sp-9 an-49 4043 ac-9 ta-67 sp-9 an-67 4044 ac-9 ta-88 sp-9 an-88 4045 ac-9 ta-89 sp-9 an-89 4046 ac-9 ta-98 sp-9 an-98 4047 ac-9 ta-99 sp-9 an-99 4048 ac-9 ta-100 sp-9 an-100 4049 ac-9 ta-101 sp-9 an-101 4050 ac-9 ta-107 sp-9 an-107 4051 ac-9 ta-115 sp-9 an-115 4052 ac-9 ta-287 sp-9 an-287 4053 ac-9 ta-288 sp-9 an-288 4054 ac-9 ta-289 sp-9 an-289 4055 ac-9 ta-290 sp-9 an-290 4056 ac-9 ta-291 sp-9 an-291 4057 ac-9 ta-292 sp-9 an-292 4058 ac-9 ta-293 sp-9 an-293 4059 ac-9 ta-294 sp-9 an-294 4060 ac-9 ta-295 sp-9 an-295 4061 ac-9 ta-296 sp-9 an-296 4062 ac-9 ta-297 sp-9 an-297 4063 ac-9 ta-298 sp-9 an-298 4064 ac-9 ta-299 sp-9 an-299 End of Table 3

Test Example 1

Blood cholesterol lowering effect in rats fed on a high cholesterol diet

In the test example, blood cholesterol lowering effect in rats fed on a high cholesterol diet was tested according to the method described in J. Lipid, Res., 1995, 36, 10981105.

That is, a diet containing 0.4% cholesterol and 0.5% of bile acid was given to 7 to 9 weeks old SD (IGS) male rats for 5 days before the test to increase the blood cholesterol level. Rats that showed an evident increase in blood cholesterol level as compared with that before feeding were selected and used in the test. Cholestimide (trade name: CHOLEBINE GRANULE 70% manufactured by MITSUBISHI TOKYO PHARMACEUTICALS, INC.), which is an anion exchange resin, was suspended in distilled water while the test compound was either dissolved or suspended in distilled water. These were forcibly orally administered twice a day every day from the day of beginning of the test (each n=8). After 3 hours from the administration of drug on the last day of the test, a blood sample was taken from a jugular vein pool and serum cholesterol level was measured to study the effect of the test compound. Further, as a control group, a group (n=8) fed on only high cholesterol diet and given distilled water was prepared and the same test procedure was followed. A commercially available kit was used for measurement of total cholesterol and HDL cholesterol. The value obtained by subtracting an HDL cholesterol value from the total cholesterol value was taken as an LDL+VLDL cholesterol value. Assuming the LDL+VLDL cholesterol value of the control group, for which the test compound was not used, as 100%, the rate of decrease (percentage of decrease) of LDL+VLDL cholesterol value when a fixed amount of the test compound was used, was determined.

The results are shown in Table 5 below. It has been verified that the compounds of the present invention decrease the LDL+VLDL cholesterol level and have excellent blood cholesterol lowering effect. Therefore, the compounds of the present invention have proved to be useful as drugs for the treatment and prevention of hyperlipidemia. Further, it has been verified that the compounds of the present invention have an inhibitory effect on increase of cholesterol even when a diet containing 0.4% cholesterol and 0.5% bile acid is fed and at the same time the compound of the present invention was forcibly orally administered, so that the compounds of the present invention are useful as drug for the prevention-of hyperlipidemia. Note that it has also been verified that the compounds of other examples of the present invention not shown in Table below have excellent blood cholesterol lowering effect and thus the compounds have proved to be useful in particular as drugs for the treatment and prevention of hyperlipidemia. TABLE 169 Rat model loaded with diet containing cholesterol (treatment model) Rate of decrease (%) of LDL + VLDL Dosage of medicine at a time is Compound in example indicated in parenthesis Comparative Example* 29.0 (25 mg/kg) Example 1 68.4 (1 mg/kg) *Cholestimide (trade name: CHOLEBINE KARYU 70% manufactured by MITSUBISHI TOKYO PHARMACEUTICALS, INC.) was used in the comparative example.

Test Example 2

Bile acid decreasing effect in portal vein of rats loaded with cholic acid

In this test example, the test for confirming the bile acid decreasing effect in portal vein of cholic acid-loaded rats was carried out according to the method described in Pharmacology and Therapeutics [Jpn Pharmacol. Ther., Vol. 24 Supplement, 1996, 103 (S-577)-110 (S-584)].

That is, 7 to 9 weeks old SD (IGS) rats were starved on the day before the test and thereafter. Cholic acid (200 mg/kg) and the test compound as drug to be administered, were either dissolved or suspended in distilled water containing a surfactant (trade name: Tween 20, BIO-RAD or HCO-60, manufactured by NIPPON CHEMICALS COMPANY, LTD.) to a final concentration of 0.5% or 1% and the solution was forcibly orally administered to the rats. After 2 hours from the administration, a sample of blood was taken from a portal vein and total blood serum bile acid level was measured to study the effect of the test compound (n=6). Further, as a control group, a group (n=6) loaded with cholic acid (200 mg/kg) only was prepared and the same test procedure was followed. A commercially available kit was used for the measurement of bile acid (trade name: SOTANJUSAN—TEST WAKO—(SOTANJUSAN=total bile acid), manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.). Assuming the value of the control group, which is a group in which no test compound was used, as 100%, the rate of decrease (percentage (%) of decrease) of the bile acid level when a fixed amount of the test compound was used was determined.

The results are shown in Table below. It has been verified that the compounds of the present invention decrease the bile acid level and proved to have excellent bile acid resorption inhibiting effect. Therefore, it has been verified that the compounds of the present invention are useful as drugs for the treatment and prevention of hyperlipidemia and further useful as drugs for the treatment of cholestasis-accompanying hepatopathy. Further, it has also been verified that the compounds of other examples of the present invention not described in Table 6 below have excellent bile acid resorption inhibiting effects and thus the compounds of the present invention have proved to be useful as drugs for the treatment and prevention of hyperlipidemia and as drugs for the therapy of cholestasis-accompanying hepatopathy. TABLE 170 Rat model loaded with cholic acid Rate of decrease (%) of bile acid Dosage of medicine at a time is Compound in example indicated in parenthesis Comparative Example 1* 16 (25 mg/kg) # Comparative Example 2** 3 (0.1 mg/kg) # Example 3835 23 (0.1 mg/kg) # Example 1 51 (0.1 mg/kg) # Example 3932 30 (0.1 mg/kg) # Example 9 13 (0.1 mg/kg) # Example 425 21 (0.1 mg/kg) # *Cholestimide (trade name: CHOLEBINE KARYU (GRANULATED POWDER) 70% manufactured by MITSUBISHI TOKYO PHARMACEUTICALS, INC.) was used in the example 1 for comparison. **A compound 5 that shows the strongest activity among compounds described specifically in WO02/08211 (synthesis example 19); 1-{4-[4-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzo-thiazepin-5-yl)phenoxymethyl]benzyl}-4-aza-1-azoniabicyclo[2.2.2]octance bromide (compound A mentioned later was used). POWDER) 70% manufactured by MITSUBISHI TOKYO PHARMACEUTICALS, INC.) was used in the example 1 for comparison. **) A compound 5 that shows the strongest activity among compounds described specifically in WO02/08211 (synthesis example 19); 1-{4-[4-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzo-thiazepin-5-yl)phenoxymethyl]benzyl}-4-aza-1-azoniabicyclo[2.2.2]octane bromide (compound A mentioned later was used).

Test Example 3

In vitro assay of compounds inhibiting ileal bile acid transporter (IBAT) using Caco-2 cells

In this test example, the in vitro assay of compounds inhibiting ileal bile acid transporter using Caco-2 cell was carried out according to the Test Example 1 described in WO00/35889.

That is, 1×10⁻⁵ cells/well Caco-2 cells were inoculated on a 24-well cell plate. For the assay, cells cultured for 14 days or more were used and the following procedure was followed. The cells were washed once with an assay buffer, Hank's buffer solution containing 25 mM glucose and with 10 mM HEPES (pH 7.4), and then the buffer was replaced by an assay buffer to which the test compound was added. After adding [³H] taurocholate (trade name: NET-322, manufactured by DAIICHI CHEMICAL CO., LTD.) to a final concentration of 8 μM, the cells were incubated at 37° C. for 30 minutes to allow [³H] taurocholate to be incorporated in Caco-2 cells by IBAT. The reaction was stopped by washing twice with a buffer prepared by adding 1 mM taurocholate (trade name: T-4009, manufactured by SIGMA) to the assay buffer and lyzing the cells with 0.2 M NaOH. Measurement of the radioactivity was carried out by introducing the cell lyzate in 4 ml of liquid scintillation cocktail (trade name: Clearzol 1, manufactured by NACALAITESC), stirring the mixture well, and then measuring the radioactivity on a liquid scintillation counter (manufactured by PACKARD CO., LTD.). The inhibition rate (%) was determined from the radioactivity of a control that did not use the test compound and the radioactivity when the test compound having a fixed concentration was used and the concentration of the test compound at which 50% of the IBAT activity was inhibited was determined. This method has verified that the compounds of the present invention have potent inhibiting activity against IBAT, so that the compounds of the present invention have proven to be useful as drugs for the treatment and prevention of hyperlipidemia.

Test Example 4

In vitro assay of compounds that inhibit temporarily expressed human IBAT transporter or rat IBAT transporter using Cos 7 cells

In this test example, the in vitro assay of the compounds that inhibit temporarily expressed human IBAT transporter or rat IBAT transporter using Cos cells was carried out according to the method described in Am. J. Physiol., 274, G157-169.

That is, 2.5×10⁻⁵ cells/well Cos 7 were inoculated on a 24-well cell plate. One day later, 0.3 μg per well of cDNA of a human IBAT or a rat IBAT was transfected by using FuGENE6 (manufactured by ROCHE PHARMACEUTICAL CO., LTD.). For the assay, the cells cultured for one day after the transfection were used and the following procedure was followed. The cells were washed once with an assay buffer, Hank's buffer solution containing 25 mM glucose and with 10 mM HEPES (pH 7.4), and then the assay buffer was replaced by an assay buffer to which the test compound was added. After adding [³H] taurocholate to a final concentration of 8 μM, the cells were incubated at 37° C. for 60 minutes. [³H] taurocholate was allowed to be incorporated in Cos 7 cells through human IBAT or rat IBAT. The reaction was stopped by washing twice with a buffer prepared by adding 1 mM taurocholate to the assay buffer and lyzing the cells with 0.2M NaOH. Measurement of radioactivity was carried out by introducing the cell lyzate in 4 ml of liquid scintillation cocktail, stirring the mixture well, and then measuring the radioactivity by a scintillation counter. The inhibition rate (%) was determined from the radioactivity of a control that did not use the test compound and the radioactivity when the test compound having a fixed concentration was used. The concentration of the test compound at which 50% of human IBAT activity or rat IBAT activity was inhibited was determined.

The results are shown in Table below. It has been verified that the compounds of the present invention have potent inhibitory activity against human IBAT and rat IBAT. Therefore, the compounds of the present invention have proven to be useful as drugs for the treatment and prevention of hyperlipidemia. Further, it has also been verified that the compounds of other examples of the present invention not shown in the Table have potent inhibition activity against human IBAT and rat IBAT. TABLE 171 Cos 7 human IBAT Cos 7 rat IBAT Compound of Example IC₅₀ (μM) IC₅₀ (μM) Comparative Example* 10 0.2 Example 3835 0.043 Not tested Example 1 0.025 0.007 Example 3932 0.036 0.009 Example 9 0.076 0.036 Example 425 0.17 Not tested Example 801 0.1 Not tested Example 1056 0.1 Not tested Example 1178 0.093 Not tested Example 1433 0.103 Not tested Example 1555 0.153 Not tested Example 1810 0.167 Not tested *The compound in synthesis example 1 described in WO93/16055: (-)-trans-3-butyl-3-ethyl-2,3,4,5-tetrahydro-5-phenyl-1,4-benzothio-azepine-1,1-dioxide was used as the comparative example.

Test Example 5

In vitro assay of compounds inhibiting temporarily expressed human IBAT transporter in which alanine 171 was substituted by serine using Cos 7 cells

The in vitro assay of the compounds inhibiting temporarily expressed human IBAT transporter in which alanine 171 was substituted with serine was carried out in the same manner as in Test Example 4 except for using the cDNA of IBAT in which alanine 171 was substituted by serine in the human IBAT amino acid sequence.

Note that actually in the case of humans, the proportion of individuals having the IBAT transporter in which alanine 171 has been substituted by serine is said to be 28% [J. Clin. Invest., 1997, 99, 1880-1887].

The results are shown in Table below. The value is a rate of inhibition (%) of the radioactivity of the test compound at a test compound concentration of 10 nM with respect to the radioactivity of the control without the test compound. It has been verified that the compound of the present invention has a potent inhibiting activity on the human IBAT in which alanine 171 is substituted by serine that is equivalent to that of the human IBAT in which alanine 171 is not substituted by serine. Therefore, the compound has proven to be useful as a drug for the treatment and prevention of hyperlipidemia. Further, it has been verified that the compounds of other examples of the present invention not shown in the Table have inhibiting activity against the human. IBAT in which alanine 171 is substituted by serine. TABLE 172 Cos 7, human IBAT in which alanine 171 is substituted by serine Rate of inhibition (%) at a test Compound of example compound concentration of 10 nM Example 1 53

Test Example 6

In vitro assay of effects of compounds on Na⁺ dependent amino acid transporter and Na⁺ dependent water-soluble vitamin transporter using Cos 7 cells

In this test example, the in vitro assays of the compound on various transporters using Cos 7 cells were carried out according to the method described in Published Translation of Japanese Patent Publication No. 10-503830.

That is, 2.5×10⁻⁵ cells/well of Cos 7 cells were inoculated on a 24-well cell plate. Two days later, the cells were washed once with an assay buffer, Hank's buffer solution containing 25 mM glucose and with 10 mM HEPES (pH 7.4), and then the buffer was replaced by an assay buffer to which the test compound was added. After adding to this, [³H] alanine (trade name; NET-348, manufactured by DAIICHI CHEMICAL CO., LTD.), [³H] leucine (trade name: NET-460, manufactured by DAIICHI CHEMICAL CO., LTD.), [³H] phenylalanine (trade name: MT903, MORAVEK), [³H] methionine (trade name: MT862, MORAVEK), [³H] lysine (trade name: MT909, MORAKEK), or [³H] choline (trade name: TRK593, AMERSHAM BIOSCIENCES CO., LTD.) to a final concentration of 8 μM, the mixture was incubated at 37° C. for 60 minutes to allow Cos 7 cells to incorporate them. The reaction was stopped by washing the cells twice with assay buffer and then lyzing them with 0.2 M NaOH. Measurement of the radioactivity was carried out by introducing the lyzate in 4 ml of liquid scintillation cocktail, stirring the mixture well, and then measuring on a liquid scintillation counter. The inhibition rate (%) was determined from the radioactivity of a control without test compounds and the radioactivity when the test compound having a fixed concentration was used, and then the concentration of the test compound at which 50% of the transporter activity was inhibited was determined.

In the small intestine epithelial cells having IBAT therein, there are also Na⁺ dependent transporters, which further include an amino acid transporter and a water-soluble vitamin transporter. Essential amino acids are indispensable for normal growth and healthy life support [TOKYO KAGAKU DOZIN CO., LTD., 2nd edition of SEIKAGAKU JITEN (Dictionary of Biochemistry), P1052]. Choline is a water-soluble vitamin, deficiency of which in human body causes fatty liver and hepatocirrhosis [TOKYO KAGAKU DOZIN CO., LTD., 2nd edition, SEIKAGAKU JITEN (Dictionary of Biochemistry), P1050].

The results are shown in Table 14. It has been verified that the compound of the present invention has significant inhibitory peculiarity against human IBAT and rat IBAT and has proven to be able to be a drug for the treatment and prevention of hyperlipidemia. Similar effects were obtained for other amino acids, such as leucine, phenylalanine, methionine, and lysine, and even choline, which is a water-soluble vitamin. Further, it has also been verified that compounds of other examples of the present invention have significant inhibitory specificities against human IBAT and rat IBAT. TABLE 173 Compound of Example IC₅₀ (μM) against alanine transporter Example 1 33

Test Example 7

Cholestasis-Accompanying Hepatopathy Model

The “cholestasis-accompanying hepatopathy” model in this test example was handled by referring to apoptosis induction in liver cells of hypercholesterolemia model described in [Am. J. Physiol., 1995, 268, G613-G621].

That is, a diet containing 0.4% of cholesterol and 0.5% of bile acid was given to 7 to 9 weeks old SD (IGS) male rats for 4 days. The test compounds were forcibly orally administered twice a day everyday from the day of starting of feeding with the high cholesterol diet (n=8). As a control group, a group (n=8) fed with only the high cholesterol diet was prepared. After 3 hours from the administration of drug on the last day of the experiment, the livers were extracted from the rats immediately after bloodletting from the abdominal aorta and fixed with a 10% neutral buffered formalin solution (trade name: FA-F96 manufactured by KOKUSAN CHEMICAL CO, LTD.). After the fixation, the livers were dewatered and embedded by use of a closed automatic embedding apparatus (trade name: ETP-180B, manufactured by SAKURA CO., LTD.) and thin slices of a thickness within the range of 2 μm to 5 μm were prepared with a microtome (trade name; IVS-410, manufactured by SAKURA CO., LTD.). Then, hematoxylin-eosin staining was performed on these thin sections using an automatic dyeing apparatus (trade name: DRS-60, manufactured by SAKURA CO., LTD.). Total number of mitotic cells in each slice was obtained by measuring for each section the number of mitotic cells at 10 different places in an area of 200 μm×200 μm in the same section.

The results are shown in Table below. It has been verified that the compounds of the present invention exhibit a decreased number of mitotic cells in the liver and have effects of ameliorating cholestasis-accompanying hepatopathy. Therefore, the compounds of the present invention have proven to be useful as drugs for the treatment and prevention of cholestasis-accompanying hepatopathy. TABLE 174 Number of mitotic cells in liver (average ± standard error, n = 8) In parenthesis, dosage of drug at a Compound of Example time is indicated. Example 1 50 ± 13 (control group) 28 ± 7 (1 mg/kg) 36 ± 13 (0.1 mg/kg)

Test Example 8

“Cholestasis-accompanying hepatopathy” Model

The “cholestasis-accompanying hepatopathy” model in this test example was handled by referring to the method by Kanno et al. [Kanzo (Liver) 43 Suppl (1): Al 26, 2002].

That is, the abdomen of a 7 to 10 weeks old SD (IGS) male rat was cut open under anesthesia with pentobarbital and partial ligation surgery of the bile duct was carried out. A blood sample was taken from the femoral vein before the surgery and this was taken as pre-administration value. The test compound and 200 mg/kg of bile acid were forcibly orally administered twice a day for 3.5 days from the next day of the surgery (protocol A). The test compound and 200 mg/kg of bile acid were forcibly orally administered twice a day for 3.5 days without carrying out the partial ligation surgery (protocol B). In both the cases, the test compound was dissolved or suspended in distilled water or an aqueous solution of 1% HCO60 (manufactured by NIPPON CHEMICALS COMPANY, LTD.). Physiological saline was administered to a control group, while 25 mg/kg of cholestyramine (manufactured by SIGMA) or 50 mg/kg of ursodeoxycholic acid (manufactured by MITSUBISHI PHARMA CO., LTD.) as a comparative example was administered. Further, to consider the influence of the surgery, a pseudo operation group (a Sham group) was established as necessary. After 6 hours from the administration of the drug on the last day of the test, a blood sample was taken from the abdominal aorta and AST (GOT), ALT (GPT), and ALP in the blood were measured by using the measurement kit (GOTII-HA TEST WAKO, GPTII-HATESTWAKO, and ALKALINE PHOSPHER-HATEST WAKO respectively, all manufactured by WAKO PURE CHEMICAL INDUSTRIES, LTD.) with an auto analyzer (NITTECH ANALYZER SUPER Z818).

The results are shown in Tables below. It has been verified that the compounds of the present invention inhibit the rise in AST, ALT, and ALP caused by partial ligation of the liver and loading of bile acid and have effects of ameliorating cholestasis-accompanying hepatopathy. Therefore, the compounds of the present invention have proved to be useful as drugs for the treatment and prevention of cholestasis-accompanying hepatopathy, in particular as drugs for the treatment and prevention of primary biliary cirrhosis and primary sclerosing cholangitis. Further, it has also been verified that the compounds of other examples of the present invention not shown in Tables 8 to 10 have excellent ameliorating effect on cholestasis-accompanying hepatopathy. TABLE 175 (Protocol A) Compound of AST ALT ALP example (IU/L) (IU/L) (IU/L) (Pre-administration 108 ± 6  38 ± 2 591 ± 116 value) Control group 400 ± 160 200 ± 81 1120 ± 410  Comparative 385 ± 214  208 ± 123 1280 ± 660  Example 1 Comparative 256 ± 64   98 ± 25 785 ± 120 Example 2 Example 1 182 ± 42  61 ± 4 603 ± 78  (0.1 mg/kg)

(For all the cases, N=8, average±standard error) In Comparative Example 1, 25 mg/kg of cholestyramine was administered while in Comparative Example 2, 50 mg/kg of ursodeoxycholic acid was administered. Distilled water was used as a solvent. TABLE 176 (Protocol B) Compound of Example AST (IU/L) ALT (IU/L) ALP (IU/L) (Pre-administration 102 ± 5  38 ± 5 508 ± 54 value) Control group 157 ± 35  82 ± 17 593 ± 77 Comparative 149 ± 10 70 ± 6 602 ± 78 Example 1 Comparative 109 ± 11 62 ± 9 453 ± 58 Example 2 Example 1 100 ± 2  53 ± 6 453 ± 50 (0.1 mg/kg) (For all the cases, N=8, average±standard error) In Comparative Example 1, 25 mg/kg of cholestyramine and in Comparative Example 2, 50 mg/kg of ursodeoxycholic acid was administered. Distilled water was used as solvent.

Test Example 9

Effect on Rat Liver Cholesterol 7α-hydroxylase Activity (7α-Ohase)

In this test example, the test for confirming the effect on rat liver cholesterol 7-α-hydroxylase activity (7α-Ohase) was carried out according to the method described in [Analytical Biochemistry, 1986, 158, 228-232].

That is, the test compound and vehicle (injectable water, trade name: manufactured by OHTSUKA PHARMACEUTICAL CO., LTD.) were administered to 6 weeks old SD (IGS) rats using an oral sonde for 14 days (n=5). Solid diet (trade name: CRF-1, manufactured by ORIENTAL YEAST CO., LTD.) was given as a diet and a sterilized tap water was given as drink water and the rats were allowed to take them freely. The rats were dissected and the livers were extracted. The livers were preserved temporarily at −80° C. Thawed liver samples were homogenized in 1.15% KCl and then centrifuged to prepare liver microsomes. Final pelletized materials were resuspended in a buffer solution of sodium phosphate/potassium phosphate, followed by incubation of an aliquot at 37° C. for 20 minutes in the presence of NADPH. The 7α-hydroxy-cholesterol formed was converted into 7α-hydroxy-4-cholesten-3-one by cholesterol oxidase. After extraction of this in petroleum ether, the organic solvent was evaporated and the residue was dissolved in isopropanol. An enzyme product was separated by injecting the aliquot of the extract into a reverse phase HPLC column (trade name: Finepack SIL-5, JASCO) and the substance eluted was quantated by using a 240 nm UV detector.

It has been verified that the compounds of the present invention have potent enhancing effects on the activity of liver cholesterol 7α-hydroxylase (7α-Ohase) that is included in the mechanism of blood cholesterol lowering effects (Arterioscler Thromb Vasc. Biol., 1998, 18, 1304-1311) due to IBAT, which is an ileal bile acid transporter and that the compounds of the present invention can be used as drugs for the treatment and prevention of hyperlipidemia and so forth.

Test Example 10

Microbial Mutagenicity (Ames Test)

In this test example, the microbial mutagenicity test was carried out according to Ames Salmonella Mutation Assay.

The strains used are Salmonella typhimurium TA98 and Salmonella typhimurium TA100 strains. In an L-shaped tube containing a sterilized preculture medium (trade name: Nutrient Broth No. 2, manufactured by KANTO KAGAKU) was added a loopful of Salmonella typhimurium TA98 or Salmonella typhimurium TA100, which then was cultured in a shaking incubator at 37° C., for 8 hours with 100 shakes per minute. 0.1 ml of this microbial culture broth was added to 2 ml of sterilized soft agar warmed at 45° C., containing 0.05 mM of L-histidine and 0.05 mM (+)-biotin. After stirring, the mixture was spread on a minimum glucose agar plate medium (trade name: TESMEDIA AN, manufactured by ORIENTAL YEAST CO., LTD.) in a Petri dish and allowed to solidify. A circular filter paper was made by punching a filter paper (trade name: Quantitative Ashless No. 7, manufactured by ADVANTECH COMPANY, LTD.), sterilized, and disposed on the solidified agar. Then, 1 μl of the test compound having a concentration of 10 mM was put on the filter paper and culturing was performed at 37° C. for 48 hours. For the judgment of the microbial mutagenicity, the occurrence of a mutant colony centered on the filter paper where the test compound was diffused was judged as positive and no occurrence of mutant colonies in that area was judged as negative.

As a result, it has been verified that all the compounds of the examples of the present invention were negative on both TA98 and TA100 in the microbial mutagenicity test (Ames test) and have no mutagenicity. Thus, the compounds of the present invention have proven to be safe. Therefore, it has been indicated that the compounds of the present invention can be drugs for the treatment and prevention of hyperlipidemia.

[Effects due to the Invention]

Since 1,4-benzothiazepine skeleton, which is a basic skeleton of the compound in the present invention, has a basic nitrogen at the 4-position, which is a position adjacent to the asymmetric center, it is easy to acquire an optically active substance by an optical resolution agent such as camphorsulfonic acid derivative and tartaric acid derivatives. Further, due to the presence of this basic nitrogen, pharmaceutically acceptable salts of various acids are formed. Since it is possible to acquire compounds that are readily soluble in water, this skeleton is a useful basic skeleton in the manufacture of pharmaceuticals. The compounds of the present invention, in which a thioamide bond and a quaternary ammonium substituent are introduced to this skeleton, are novel compounds and have very potent ileal bile acid transporter inhibiting activities as compared to the other known compounds having this skeleton. Further, the compounds of the present invention have stability such that they are difficultly metabolized in vivo and have reduced toxicity to an alimentary canal. According to the test examples mentioned above, the compounds are useful as cholesterol lowering agents and have been confirmed to be useful as pharmaceutical compositions for the treatment and prevention of hyperlipidemia, arteriosclerosis, syndrome X etc. Further, the compounds of the present invention are also useful as curing agents for cholestasis-accompanying hepatopathy and have been confirmed to be useful as pharmaceutical compositions for the treatment and prevention of cholestasis-accompanying hepatopathy, particularly for the treatment and prevention of primary biliary cirrhosis and primary sclerosing cholangitis. The compounds of the present invention have been confirmed to be useful as pharmaceutical compositions for the treatment and prevention of obesity and fatty liver. 

1. A compound represented by formula (1) below.

[wherein R¹ and R², which may be mutually different, each represents an alkyl group having from 1 to 10 carbon atoms; m represents an integer of 1 or 2, and R³ and R⁴, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms; Y represents any one of —NHCS—, —NHCSNH—, and —NHCSO— where the —NH in the —NHCS— represents a bond which links with an adjacent benzene ring and the CS— in the —NHCS— represents a bond which links with an adjacent Z, and the —NH in the —NHCSO— represents a bond which links with an adjacent benzene ring and the CSO— in the —NHCSO— represents a bond which links with an adjacent Z; Z—(N⁺R⁵R⁶R⁷)_(n) represents an alkyl group having from 2 to 10 carbon atoms or an alkenyl group having from 2 to 10 carbon atoms which is substituted with n (—N⁺R⁵R⁶R⁷)s, where at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—; n is an integer of 1 or 2; and N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent I) R⁵, R⁶, and R⁷, which may be mutually different, each represents any one of an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, and an alkynyl group having from 2 to 10 carbon atoms, where the alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, an —SO₃H group, and further, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰— where R⁸ represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms and the alkyl group and alkenyl group represented by R⁸ may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group; R⁹ and R¹⁰, which may be mutually different, each represents an alkyl group or alkenyl group having from 1 to 5 carbon atoms and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group; and W⁻ represents a counter anion, II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is formed by 4 to 9 carbon atoms in addition to an ammonium nitrogen atom, provided that the position of its bonding with Z is the ammonium nitrogen atom, where one of the carbon atoms which constitute the ring in the monocyclic ring and the bicyclic ring may be replaced by any one atom of oxygen, nitrogen, and sulfur, and moreover, the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a thioxo group, a cyano group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an —R¹¹ group; R¹¹ represents an alkyl group having from 1 to 8 carbon atoms or an alkenyl group having from 2 to 8 carbon atoms, where the alkyl group and the alkenyl group represented by R¹¹ may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group; moreover, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—, where R⁸, R⁹, R¹⁰, and W⁻ are as described above; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the monocyclic ring and the bicyclic ring is the same as that in I) described above, III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the pyridinium ring, the quinolinium ring, and the isoquinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, an alkoxy group having from 1 to 5 carbon atoms, a carboxyl group, a —CONH₂ group, an —SO₃H group, and an —R¹² group; R¹² represents an alkyl group having from 1 to 9 carbon atoms or an alkenyl group having from 2 to 9 carbon atoms; and the alkyl group and the alkenyl group represented by R¹² may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group; and further, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —S—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰—, where R⁸, R⁹, R¹⁰, and W⁻ are as described above, and X⁻ represents a counter anion].
 2. The compound according to claim 1, wherein the Z—(N⁺R⁵R⁶R⁷)_(n) represents an alkyl group having from 2 to 10 carbon atoms which is substituted with n (—N⁺R⁵R⁶R⁷)s and at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—.
 3. The compound according to claim 2, wherein the Z—(N⁺R⁵R⁶R⁷)_(n) represents a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷ and at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—.
 4. The compound according to claim 3, wherein the Z—(N⁺R⁵R⁶R⁷)_(n) represents a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷, a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷ and one of methylenes which constitute Z is replaced by a phenylene, a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷ and one of methylenes which constitute Z is replaced by an —O—, or a straight chain alkyl group having from 2 to 10 carbon atoms which is substituted with one —N⁺R⁵R⁶R⁷ and one of methylenes which constitute Z is replaced by a phenylene and another of methylenes which constitute Z is replaced by an —O—.
 5. The compound according to claim 4, wherein Z represents a straight chain methylene group having from 2 to 10 carbon atoms, a straight chain methylene group having from 2 to 10 carbon atoms of which one methylene is replaced by a phenylene, a straight chain methylene group having from 2 to 10 carbon atoms of which one methylene is replaced by an —O—, or a straight chain methylene group having from 2 to 10 carbon atoms of which one methylene is replaced by a phenylene and another methylene is replaced by an —O—.
 6. The compound according to claim 5, wherein Z represents a straight chain methylene group having from 2 to 10 carbon atoms.
 7. The compound according to claim 5, wherein Y represents —NHCS— or —NHCSNH— at the para- or meta-position.
 8. The compound according to claim 6, wherein Y represents —NHCS— or —NHCSNH— at the para- or meta-position.
 9. The compound according to claim 8, wherein Y represents —NHCSNH— at the meta-position; and Z represents a straight chain methylene group having from 2 to 10 carbon atoms.
 10. The compound according to claim 8, wherein Y represents —NHCS— at the meta-position; and Z represents a straight chain methylene group having from 2 to 10 carbon atoms.
 11. The compound according to claim 10, wherein Y represents —NHCS— at the meta-position; and Z represents a straight chain methylene group having 5 carbon atoms.
 12. The compound according to claim 5, wherein Y represents —NHCSNH— at the meta-position; and Z represents a straight chain methylene group having from 2 to 10 carbon atoms of which one methylene is replaced by a phenylene.
 13. The compound according to claim 8, wherein Y represents —NHCS— or —NHCSNH— at the meta-position; and Z is represented by formula (sp-14)

[wherein *a is bonded to Y in the formula (1) and *b is bonded to N⁺R⁵R⁶R⁷].
 14. The compound according to claim 12, wherein Y represents —NHCSNH— at the meta-position; and Z is represented by formula (sp-14)

[wherein *a is bonded to Y in the formula (1) and *b is bonded to N⁺R⁵R⁶R⁷].
 15. The compound according to claim 1, wherein N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent: I) R⁵, R⁶, and R⁷, which may be mutually different, each represents any one of an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 3 to 8 carbon atoms, and an alkynyl group having from 3 to 9 carbon atoms, where the alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, and further, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, an —O—, a —CO₂—, an —NHCO—, an —NR⁸—, and an —N⁺W⁻R⁹R¹⁰— where R⁸ represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group; R⁹ and R¹⁰, which may be mutually different, each represents an alkyl group having from 1 to 3 carbon atoms or an alkenyl group having 3 carbon atoms and the alkyl group may be substituted with at least one of a phenyl group and a hydroxyl group, II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is any one of a pyrrolidinium ring, a piperidinium ring, a morpholinium ring, a thiomorpholinium ring, a piperazinium ring, an azepanium ring, a quinuclidinium ring, and a 1,4-diazabicyclo[2.2.2]octanium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂ group, and an —R¹¹ group; R¹¹ represents an alkyl group having from 1 to 6 carbon atoms or an alkenyl group having 3 carbon atoms, where the alkyl group represented by R¹¹ may be substituted with at least one of a hydroxyl group, a cyano group, a phenyl group, and a —CONH₂ group; moreover, at least one of methylenes which constitute the alkyl group may be replaced by any one of an —O—, a —CO₂—, and an —NHCO—; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the ring represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, or an alkynyl group having 3 to 6 carbon atoms; the alkyl group, the alkenyl group, and the alkynyl group represented by R⁵, R⁶, or R⁷ may be substituted with at least one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, an oxo group, a nitro group, a carboxyl group, an —CONH₂ group, and an —SO₃H group; and moreover, at least one of methylenes which constitute the alkyl group may be replaced by any one of a phenylene, an —O—, and a —CO₂—, III) N⁺R⁵R⁶R⁷ represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the pyridinium ring and the quinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a thienyl group, a pyridyl group, an alkoxy group having from 1 to 3 carbon atoms, a carboxyl group, a —CONH₂ group, and an —R¹² group; R¹² represents an alkyl group having from 1 to 9 carbon atoms or an alkenyl group having from 2 to 4 carbon atoms; and the alkyl group and the alkenyl group represented by R¹² may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a cyano group, a nitro group, a hydroxyl group, an oxo group, a carboxyl group, and an —SO₃H group; and further, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of an —S—, a —CO₂—, an —NHCO—, and an —NR⁸— where R⁸ represents an alkyl group having 1 to 3 carbon atoms and the alkyl group may be substituted with at least one hydroxyl group.
 16. The compound according to claim 1, wherein N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent: I) R⁵, R⁶, and R⁷, which may be mutually different, each represents a straight chain alkyl group having from 1 to 10 carbon atoms, a straight chain alkenyl group having from 3 to 6, or 8 carbon atoms, a branched alkenyl group having 4, 6, or 7 carbon atoms, a straight chain alkynyl group having from 3, 5, 6, 7, or 9 carbon atoms, or a branched alkynyl group having 6 carbon atoms, in which 1) the alkyl group, alkenyl group, and alkynyl group represented by R⁵, R⁶, and R⁷ are substituted with any one of a phenyl group, a thienyl group, a cyclohexyl group, a cyano group, a hydroxyl group, an oxo group, a carboxyl group, a —CONH₂ group, and an —SO₃H group, 2) the alkyl group, the alkenyl group, and the alkynyl group are substituted with two hydroxyl groups, 3) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and one —SO₃H group, 4) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group and one phenyl group, 5) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and two phenyl groups, 6) one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by any one of a phenylene, a furylene, a —CO₂—, an —NHCO—, an —NR⁸— (where R⁸ represents a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, a 2-hydroxypropyl group, or a benzyl group), and an —N⁺W⁻R⁹R¹⁰— (where R⁹ and R¹⁰ each represents a methyl group, an ethyl group, an n-propyl group, a 2-propenyl group, a 2-hydroxyethyl group, or a benzyl group), 7) two of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by any one selected from two (—O—)s, one phenylene and one —O—, one —O— and one —NR⁸—, and one —NHCO— and one —O—, 8) three of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by any one selected from two (—O—)s and one —NR⁸—, or one phenylene and two (—NHCO—)s, 9) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —O—, 10) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —NR⁸—, 11) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group, and moreover one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a furylene, 12) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group, and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a thienylene, or 13) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one oxo group, and moreover, two of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group are replaced by one —O— and one phenylene, or the alkyl group, alkenyl group, and alkynyl group are neither substituted nor replaced, II) N⁺R⁵R⁶R⁷ represents a monocyclic ring or a bicyclic ring which is any one of a pyrrolidinium ring, a piperidinium ring, a morpholinium ring, a thiomorpholinium ring, a piperazinium ring, an azepanium ring, a quinuclidinium ring, and a 1,4-diazabicyclo[2.2.2]octanium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom; the monocyclic ring and the bicyclic ring are 1) substituted with any one of a hydroxyl group, an oxo group, a cyano group, a phenyl group, a —CONH₂ group, and an —R¹¹ group, 2) substituted with one cyano group and one hydroxyl group, 3) substituted with one hydroxyl group and one —R¹¹, 4) substituted with one oxo group and one —R¹¹, 5) substituted with two oxo groups, or 6) substituted with two (—R¹¹)s, or the monocyclic ring and the bicyclic ring are unsubstituted, where R¹¹ represents any one of a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a benzyl group, an acetylamino group, a t-butoxycarbonylamino group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a 2-cyanoethoxy group, a (2-cyanoethoxy)methyl group, a 2-carbamoylethoxy group, an ethoxycarbonyl group, a t-butoxycarbonyl group, a benzoyloxy group, a phenylacetylamino group, a butanoylamino group, and a pentanoylamino group; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the ring represents a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkenyl group having from 3 to 4 carbon atoms, or a straight chain alkynyl group having 3, 4, or 6 carbon atoms, and 1) the alkyl group, the alkenyl group, and the alkynyl group represented by R⁵, R⁶, or R⁷ are substituted with any one of a phenyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cyclopropyl group, a cyclopentyl group, a cyano group, a hydroxyl group, a carboxyl group, and an —SO₃H group, 2) the alkyl group, the alkenyl group, and the alkynyl group are substituted with two hydroxyl groups, 3) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one hydroxyl group and one —SO₃H, 4) the alkyl group, the alkenyl group, and the alkynyl group are substituted with four hydroxyl groups and one oxo group, 5) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one nitro group and one morpholyl group, 6) one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by a —CO₂—, or 7) the alkyl group, the alkenyl group, and the alkynyl group are substituted with one morpholyl group and moreover, one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group is replaced by an —O—, or the alkyl group, the alkenyl group, and the alkynyl group are neither substituted nor replaced, III) N⁺R⁵R⁶R⁷ represents any one of 1) a pyridinium ring substituted with any one of a cyano group, a phenyl group, a thienyl group, a pyridyl group, a methoxy group, an ethoxy group, a propoxy group, a carboxyl group, a —CONH₂ group, and a —R¹² group, 2) a pyridinium ring substituted with two cyano groups, 3) a pyridinium ring substituted with two (—R¹²)s, 4) a pyridinium ring substituted with one cyano group and one —R¹², 5) a pyridinium ring substituted with one phenyl group and one —R¹², 6) a quinolinium ring substituted with any one of a cyano group, a nitro group, a carboxyl group, a methoxy group, an ethoxy group, a propoxy group, and —R¹², 7) a quinolinium ring substituted with one methoxy group and one —R¹², 8) a quinolinium ring substituted with one nitro group and one —R¹², 9) an unsubstituted pyridinium ring, 10) an unsubstituted quinolinium ring, and 11) an unsubstituted isoquinolinium ring, where R¹² represents any one of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a 3-pentyl group, a 5-nonyl group, a vinyl group, a benzyl group, a 3-phenylpropyl group, a 2-(1-naphthyl)vinyl group, a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxypropyl group, a formyl group, an acetyl group, a propionyl group, a benzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, a hexoxycarbonyl group, a benzyloxycarbonyl group, a 2-propenyloxycarbonyl group, an ethoxycarbonylmethyl group, a 2-(methoxycarbonyl)ethyl group, an ethoxycarbonylmethylcarbonyl group, a 2-hydroxyethylaminocarbonyl group, a bis(2-hydroxyethyl)aminocarbonyl group, a 2-carboxyvinyl group, a carboxymethylthio group, a cyanomethyl group, a 2-nitrovinyl group, a 2-(4-pyridyl)ethyl group, a 2-(4-pyridyl)vinyl group, a 3-(4-pyridyl)propyl group, a 2-(4-pyridyl)-1,2-dihydroxyethyl group, and a 2-sulfoethyl group, provided that the position of its bonding with Z is an ammonium nitrogen atom.
 17. The compound according to claim 1, wherein N⁺R⁵R⁶R⁷ is any one of I), II), and III) given below which are mutually independent: I) R⁵, R⁶, and R⁷, which may be mutually different, each represents any one of a straight chain alkyl group having from 1 to 10 carbon atoms, a straight chain alkyl group having from 1 to 10 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group having from 1 to 10 carbon atoms which is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 6, or 8 carbon atoms, a branched alkenyl group having 4, 6, or 7 carbon atoms, a straight chain alkynyl group having 3, 5, 6, 7, or 9 carbon atoms, and a branched alkynyl group having 6 carbon atoms, II) N⁺R⁵R⁶R⁷ represents a pyrrolidinium ring, a piperidinium ring, an azepanium ring, a quinuclidinium ring, or a 1,4-diazabicyclo[2.2.2]-octanium ring, substituted with any one of a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, a 2-propenyl group, a phenyl group, a benzyl group, a hydroxyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group, or unsubstituted, provided that the position of its bonding with Z is an ammonium nitrogen atom; among R⁵, R⁶, and R⁷, a group which is not involved in formation of the ring represents any one of a straight chain alkyl group having from 1 to 6 carbon atoms, a straight chain alkyl group having from 1 to 6 carbon atoms which is substituted with one phenyl group, a straight chain alkyl group having from 1 to 6 carbon atoms which is substituted with one hydroxyl group, a straight chain alkenyl group having from 3 to 4 carbon atoms, and a straight chain alkynyl group having 3, 4, or 6 carbon atoms, III) N⁺R⁵R⁶R⁷ represents an unsubstituted pyridinium ring, an unsubstituted quinolinium ring, an unsubstituted isoquinolinium ring, a pyridinium ring substituted with any one of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-pentyl group, a vinyl group, a phenyl group, a benzyl group, a 3-phenylpropyl group, a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group, a pyridinium ring substituted with any one selected from two methyl groups or two ethyl groups, a pyridinium ring substituted with one phenyl group and one methyl group, or a quinolinium ring substituted with any one of a methyl group and an i-propyl group, provided that the position of its bonding with Z is ammonium nitrogen atom.
 18. The compound according to claim 15, wherein R¹ and R², which may be mutually different, each represents a straight chain alkyl group having 2 to 6 carbon atoms, and (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7-position, an ethylmethylamino group substituting at the 7-position, a dimethylamino group substituting at the 9-position, and dimethylamino groups substituting at the 7- and 9-positions.
 19. The compound according to claim 16, wherein R¹ and R², which may be mutually different, each represents a straight chain alkyl group having 2 to 6 carbon atoms, and (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7-position, an ethylmethylamino group substituting at the 7-position, a dimethylamino group substituting at the 9-position, and dimethylamino groups substituting at the 7- and 9-positions.
 20. The compound according to claim 17, wherein R¹ and R², which may be mutually different, each represents a straight chain alkyl group having 2 to 6 carbon atoms, and (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7-position, an ethylmethylamino group substituting at the 7-position, a dimethylamino group substituting at the 9-position, and dimethylamino groups substituting at the 7- and 9-positions.
 21. The compound according to claim 18, wherein (NR³R⁴)_(m) represents any one of a dimethylamino group substituting at the 7-position, a diethylamino group substituting at the 7-position, and an ethylmethylamino group substituting at the 7-position, and N⁺R⁵R⁶R⁷ represents any one of a 4-t-butylpyridinium group, a 3-(3-hydroxypropyl)-pyridinium group, a 3-[2-(methoxycarbonyl)ethyl]-pyridinium group, a 2-(n-propyl)-pyridinium group, a 4-phenylquinuclidinium group, and a 1,4-diazabicyclo[2.2.2]octanium group.
 22. A pharmaceutical composition containing the compound according to claim 1 as an active ingredient.
 23. The pharmaceutical composition according to claim 22, wherein the pharmaceutical composition is a cholesterol-lowering agent.
 24. The pharmaceutical composition according to claim 23, wherein the pharmaceutical composition is a drug for the treatment or prevention of any one of hyperlipidemia, arteriosclerosis, and syndrome X.
 25. The pharmaceutical composition according to claim 22, wherein the pharmaceutical composition is a drug for the treatment or prevention of cholestasis-caused hepatopathy.
 26. The pharmaceutical composition according to claim 25, wherein the pharmaceutical composition is a drug for the treatment or prevention of primary biliary cirrhosis or primary sclerosing cholangitis.
 27. The pharmaceutical composition according to claim 22, wherein the pharmaceutical composition is a drug for the treatment or prevention of obesity or fatty liver.
 28. The pharmaceutical composition according to claim 22, wherein the pharmaceutical composition is a drug for the treatment or prevention of steatohepatitis.
 29. A pharmaceutical composition for the treatment or prevention of cholestasis-caused hepatopathy comprising an ileal bile acid transporter inhibiting compound as an active ingredient.
 30. The pharmaceutical composition according to claim 29, wherein the pharmaceutical composition is a drug for the treatment or prevention of any one of primary biliary cirrhosis and primary sclerosing cholangitis. 